"Tripodal europium complex with triangulenium dye: a model bifunctional metallo-organic system"
Hamacek, J.; Besnard, C.; Mehanna, N.; Lacour, J.
Dalton Trans.2012, 41, 6777-6782open archive unige:20423 full text [restricted access]
A new tripodal ligand has been designed by coupling pyridyldicarbonyl binding strands with a triazatriangulenium platform (TATA). The complexation reaction with europium provides a C3-symmetrical mononuclear compound that is characterized with NMR, ESMS and qualitatively with single-crystal X-ray crystallography. In addition, photophysical studies of this dual emissive system have been performed, since the combination of the TATA fluorophore with trivalent lanthanides is of potential interest for the further development of imaging applications.
137.
"Enol Acetal Synthesis through Carbenoid C—H Insertion into Tetrahydrofuran Catalyzed by CpRu Complexes"
Tortoreto, C.; Achard, T.; Zeghida, W.; Austeri, M.; Guénée, L.; Lacour, J.
Angew. Chem. Int. Ed.2012, in press
[CpRu(CH3CN)3][PF6] and diimine ligands catalyze the decomposition of α-diazo-β-ketoesters in THF leading to original products of 1,4-C−H insertion. In contrast with previous results, only novel enol-acetal motifs are obtained through intermolecular C-O instead of C-C bond forming reactions.
136.
"Medium-Sized Rings vs Macrocycles through Rhodium-Catalyzed Ring-Expansion Reactions of Cyclic Acetals"
Ballesteros-Garrido, R.; Rix, D.; Besnard, C.; Lacour, J.
Chem. Eur. J.2012, 18, 6626-6631open archive unige:20422 full text [restricted access]
α-Diazo β-ketoesters and diketones react with cyclic acetals under Rh(II)-catalysis to yield in one-pot unprecedented polyoxygenated 8- and 9-membered rings. The reactions occur under mild conditions with yields up to 90%. The medium-sized ring formation and perfect regioselectivity are direct consequences of Baldwin’s rules.
135.
"Surprisingly difficult resolution of N-methylated cationic [4]helicenes"
Mehanna, N.; Grass, S.; Lacour, J.
Chirality2012, in press
"Asymmetric synthesis of ethano-Tröger bases using CuTC-catalyzed diazo decomposition reactions"
Sharma, A.; Besnard, C.; Guénée, L.; Lacour, J.
Org. Biomol. Chem.2012, 10, 966-969open archive unige:18072 full text [restricted access]
Nonracemic ethano-bridged Tröger bases are prepared using CuTC-catalyzed decomposition of diazo compounds. Excellent levels of diastereo- and enantio-control (dr and ee up to 12:1 and 95% respectively) are now obtained with aryl diazoketone precursors.
132.
"Chiral anion-based NMR enantiodiscrimination of a dinuclear, cationic Ir(I) NHC complex with a figure-of-eight loop structure"
Liu, X.; Lacour, J.; Braunstein, P.
Dalton Trans.2012, 41, 138-142open archive unige:17761 full text [restricted access]
A dinuclear Ir(I) complex with a bis-NHC ligand was formed in situ from 1,1’-((4,6-dimethyl-1,3-phenylene)bis(methylene))bis(3-methyl-1H-imidazol-3-ium) in the presence of Cs2CO3 and [Ir(μ-Cl)(cod)]2. Its solid-state structure, determined by X-ray diffraction, shows a figure-of-eight loop with both the P and M enantiomers being present. Solution NMR studies were performed to examine the enantiodiscrimination between them by applying the enantiopure anions tris(tetrachlorobenzenediolato)phosphate(V) (Δ-TRISPHAT) and bis(tetrachlorobenzenediolato)mono([1,10]binaphthalenyl-2,20-diolato)phosphate(V) (Λ-BINPHAT).
"Radical cation salts of BEDT-TTF, enantiopure tetramethyl-BEDT-TTF, and TTF-Oxazoline (TTF-Ox) donors with the homoleptic TRISPHAT anion"
Riobé, F.; Piron, F.; Réthoré, C.; Madalan, A. M.; Gómez-García, C. J.; Lacour, J.; Wallis, J. D.; Avarvari, N.
New J. Chem.2011, 35, 2279-2286open archive unige:17067 full text [restricted access]
The synthesis and crystal structures of five radical cation salts based on the organic donors bis(ethylenedithio)tetrathiafulvalene, racemic ethylenedithio-methyl-oxazoline-tetrathiafulvalene and the enantiopure tetramethyl-bis(ethylenedithio)tetrathiafulvalene and the D3-symmetric anion tris(tetrachlorobenzenediolato)phosphate(V) TRISPHAT are reported. The donors are fully oxidized and self-assemble in dyads inserted in the channels generated by the packing of the TRISPHAT anions.
130.
"Macrocyclization of Oxetane Building Blocks with Diazocarbonyl Derivatives under Rhodium(II) Catalysis"
Rix, D.; Ballesteros-Garrido, R.; Zeghida, W.; Besnard, C.; Lacour, J.
Angew. Chem. Int. Ed.2011, 50, 7308-7311open archive unige:16745 full text [restricted access]
Highly concentrated: The title reaction proceeds to afford a rare type of 15-membered polyether macrocycle in up to 84 % yield (R1=alkyl, alkoxy, O-allyl, OCH2CH2Ph; R2=alkyl, Ph; R3=H, Me, Et). This nontemplated macrocyclization is performed in a single pot under high concentration and precludes the usual polymerization.
Using a two-step reduction / metalation procedure, highly stable chiral carbenium ions are transformed into reactive carbanion intermediates. Interesting polar ketone and thioamide products are the results of this umpolung that occurs with complete retention of configuration of the helical backbone.
128.
"CpRu-Catalyzed O-H Insertion and Condensation Reactions of α-Diazocarbonyl Compounds"
Austeri, M.; Rix, D.; Zeghida, W.; Lacour, J.
Org. Lett.2011, 13, 1394-1397open archive unige:14595 full text [restricted access]
[CpRu(CH3CN)3][PF6] and diimine ligands catalyze together the decomposition of α-diazoacetoacetates leading to O-H insertion and condensation reactions. In comparison with Rh(II) and Cu(I) complexes, the CpRu catalysts produce rapid and often more selective reactions. Promising enantioselectivities are obtained in dioxole syntheses.
Configurationally-stable ethano-Tröger bases are prepared in a single step via the direct Rh(II)-catalyzed reaction of methano-Tröger bases and diazo esters. The process is general, enantiospecific (ee up to 99%), diastereoselective (with a new quaternary carbon center introduction, dr up to 49:1) and regioselective.
126.
"Highly selective additions of hydride and organolithium nucleophiles to helical carbenium ions"
Guin, J.; Besnard, C.; Pattison, P.; Lacour, J.
Chem. Sci.2011, 2, 425-428open archive unige:14469 full text [restricted access]
Unsymmetrical cationic [4]helicenes react with hydride or organolithium reagents and the two diastereotopic faces can be discriminated with high efficiency (dr up to and higher than 49:1)
"(Cyclopentadienyl)ruthenium-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Etherification of Allyl Aryl and Alkyl Carbonates"
Austeri, M.; Linder, D.; Lacour, J.
Adv. Synth. Catal.2010, 352, 3339-3347open archive unige:12923
(Cyclopentadienyl)tris(acetonitrile)ruthenium hexafluorophosphate {[CpRu(NCMe)3][PF6]} or (cyclopentadienyl)(η6-naphthalene)ruthenium hexafluorophosphate {[CpRu(η6-naphthalene)][PF6]} in combination with a pyridine oxazoline ligand efficiently catalyze the decarboxylative allylic rearrangement of allyl aryl carbonates. Good levels of regio- and enantioselectivity are obtained. Starting from enantioenriched secondary carbonates, the reaction is stereospecific and the corresponding allylic ethers are obtained with net retention of configuration. An intermolecular version of this transformation was also developed using allyl alkyl carbonates as substrates. Conditions were found to obtain the corresponding products with similar selectivity as in the intramolecular process. Through the use of a hemi-labile hexacoordinated phosphate counterion, a zwitterionic air- and moisture-stable chiral ruthenium complex was synthesized and used in the enantioselective etherification reactions. This highly lipophilic metal complex can be recovered and efficiently reused in subsequent catalysis runs.
124.
"Rhodium(II)-Catalyzed One-Pot Four-Component Synthesis of Functionalized Polyether Macrocycles at High Concentration"
Zeghida, W.; Besnard, C.; Lacour, J.
Angew. Chem. Int. Ed.2010, 49, 7253-7256open archive unige:11875
[ Selected as a hot paper. Highlighted in CHIMIA Swiss Science Concentrates. ]
Against conventional wisdom, the rhodium(II)-catalyzed nontemplated macrocyclization of four separate components in one reaction vessel became more efficient as the concentration was increased. Thus, α-diazo-β-ketoesters underwent condensation with 1,4-dioxane, tetrahydrofuran, or tetrahydropyran as the solvent to yield 16- to 18-membered polyether macrocycles in up to 75 % yield (see scheme; R=Me, Et, PhCH2CH2, allyl, PhCHCH2).
123.
"On the Synthesis and Optical Properties of Sulfur-Bridged Analogues of Angulenium Cations and Derivatives"
Nicolas, C.; Bernardinelli, G.; Lacour, J.
J. Phys. Org. Chem.2010, 23, 1049-1056open archive unige:12268
"Synthesis, Resolution, and Stabilities of a Cationic Chromenoxanthene [4]helicene"
Guin, J.; Besnard, C.; Lacour, J.
Org. Lett.2010, 12, 1748-1751open archive unige:6001
1,13-Dimethoxychromenoxanthenium – a key intermediate in the synthesis of the classical trioxatriangulenium cation – was isolated and characterized for the first time. This [4]helicene was resolved through a CSP-HPLC procedure; chemical and configurational stabilities being determined and compared.
New functionalized ethano-bridged Tröger bases are readily prepared using a simple alkylation/rearrangement sequence which affords configurationally stable derivatives as single stereoisomers (de > 96%).
"Kinetic Control in the Chiral Recognition of Three-Bladed Propellers"
Bonnot, C.; Aubert, E.; Banerji, N.; Lacour, J.; Espinosa, E.; Chambron, J.-C.
Chem. Eur. J.2010, 16, 5706-5711open archive unige:6579
The ion pair of the stereolabile protonated C3-symmetric diaza-macropentacycle and the configurationally stable Δ-TRISPHAT anion exists in the form of two diastereomers. Herein, it is shown that solvent polarity controls the thermodynamics of the inversion of the cationic propeller. However, both polarity and basicity control the kinetics of exchange.
Three tricyclic (8-membered ring) diquats were prepared and shown to be the first configurationally stable derivatives of their kind. Resolution was achieved using chiral hexacoordinated phosphorus BINPHAT and TRISPHAT anions. Noticeably, these derivatives are the first eight-membered ring derivatives with only three ring constraints to be ever resolved. This manuscript also reports the first procedure to remove TRISPHAT anions after a diastereomeric separation.
Chemical reactions and processes often involve cationic reagents, intermediates or products in prochiral or chiral racemic form. To afford instead non-racemic compounds, an asymmetric ion pairing of the cations with chiral anionic counterions can be considered. This review presents recent examples of the synthesis and use of chiral anions for such stereoselective purposes.
113.
"Highly Efficient NMR Enantiodiscrimination of Chiral Octanuclear Metalla-Boxes in Polar Solvent"
Barry, N. P. E.; Austeri, M.; Lacour, J.; Therrien, B.
Organometallics2009, 28, 4894-4897open archive unige:7050 full text [restricted access]
Self-assembly tetra(4-pyridyl)porphyrins with the dinuclear p-cymene ruthenium clips affords chiral cationic organometallic boxes. In solution, these complexes assume chiral conformations and a rapid and effective enantiodifferentiation was achieved in the presence of the NMR chiral solvating agent Λ-BINPHAT anion. Only 0.05 to 0.10 equiv is necessary for complete baseline-to-baseline separation of some of the proton signals of the enantiomers. To add to this highly effective discrimination, all experiments were performed in the high-polarity solvent CD3CN, a solvent traditionally not favorable for effective chiral ion-pairing phenomena.
112.
"Vicinal diphosphoniums: electrostatic repulsion under covalent constraint"
Abdalilah, M.; Zurawinski, R.; Canac, Y.; Laleu, B.; Lacour, J.; Lepetit, C.; Magro, G.; Bernardinelli, G.; Donnadieu, B.; Duhayon, C.; Mikolajczyk, M.; Chauvin, R.
Dalton Trans.2009, 8493-8508open archive unige:7951 full text [restricted access]
A series of five vicinal bis(alkyl-triarylphosphoniums) derived from o-bis(diphenyl-phosphino)benzene (o-dppb) is described. Each of them have been prepared by specific methods, and their formal electrostatic and possible van der Waals strain is compared through the P+···P+ distances in the crystal state. (...)
111.
"Lewis Acid / CpRu Dual Catalysis in the Enantioselective Decarboxylative Allylation of Ketone Enolates"
Linder, D.; Austeri, M.; Lacour, J.
Org. Biomol. Chem.2009, 7, 4057-4061open archive unige:7960 full text [restricted access]
The addition of a Lewis acidic metal triflate salt Mg(OTf)2 as co-catalyst in the CpRu-catalyzed decarboxylative allylation of in situ-generated ketone enolates allows the reaction to proceed at lower temperature with higher regio- and enantioselectivity. Even so-far-unreactive substrates react.
110.
"Highly enantioselective biphasic iminium-catalyzed epoxidation of alkenes. On the importance of the counterion and of N(sp2)—C(sp3) rotamers"
Novikov, R.; Bernardinelli, G.; Lacour, J.
Adv. Synth. Catal.2009, 351, 596-606open archive unige:7052 full text [restricted access]
Diastereomeric biaryliminium cations made of an (Ra)-5,5’,6,6’,7,7’,8,8’-octahydrobinaphthyl core and exocyclic appendages derived from (S)- or (R)-3,3-dimethylbutan-2-amine are effective asymmetric epoxidation catalysts for unfunctionalized alkenes. Herein, we report that the negative counterion of the iminium salts has to be chosen wisely. While the hexafluoroantimonate anion [SbF6-] is optimal for reliable results, one has to be careful about other anions and tetraphenylborate [BPh4-] in particular. We also detail that the so far unexplained “lack” of stereochemical control from the chiral exocyclic appendage in this type of catalysts is due to the existence of atropisomers around the N(sp2)—C(sp3) bond that links the azepinium core to the exocyclic stereocenter. Finally, we develop a general model to predict with certainty the high selectivity in the formation of non-racemic epoxides of defined absolute configuration.
109.
"Mounting Freestanding Molecular Functions onto Surfaces: The Platform Approach"
Baisch, B.; Raffa, D.; Jung, U.; Magnussen, O. M.; Nicolas, C.; Lacour, J.; Kubitschke, J.; Herges, R.
J. Am. Chem. Soc.2009, 131, 442-443open archive unige:7043 full text [restricted access]
A modular system has been developed to mount molecules upright onto metal surfaces in a well controlled geometry. The approach is based on a reactive platform (triazatriangulenium salt) with an electrophilic center. Functional molecules are attached via C−C bond formation. The distance from the surface can be varied by a spacer, and the distance of the functional units from each other by the size of the platform. Self-assembly of the parent triazaangulenium salt as well as the functionalized platforms on Au(111) surfaces results in stable, hexagonally ordered adlayers.
108.
"Conformationally-locked metallomacrocycles – prototypes for a novel type of axial chirality"
Chow, H. S.; Constable, E. C.; Frantz, R.; Housecroft, C. E.; Lacour, J.; Neuburger, M.; Rappoport, D.; Schaffner, S.
New. J. Chem.2009, 33, 376-385open archive unige:7046 full text [restricted access]
[ Special issue dedicated to Jean-Pierre Sauvage on the occasion of his 65th birthday ]
107.
"NMR Enantiodifferentiation of Quaternary Ammonium Salts of Tröger Base"
Michon, C.; Gonçalves-Farbos, M.-H.; Lacour, J.
Chirality2009, 21, 809-817open archive unige:8004 full text [restricted access]
[ Proceedings from the 20th International Symposium on Chirality, Geneva, Switzerland, 2008 ]
"Enantioselective CpRu-Catalyzed Carroll Rearrangement. Metal Source Importance and Ligand Optimization"
Linder, D.; Buron, F.; Constant, S.; Lacour, J.
Eur. J. Org. Chem.2008, 5778-5785open archive unige:7952 full text [restricted access]
"Enantioselective and Regioselective Ru-Catalyzed Decarboxylative Etherification of Allyl Aryl Carbonates"
Austeri, M.; Linder, D.; Lacour, J.
Chem. Eur. J.2008, 14, 5737-5741open archive unige:7033 full text [restricted access]
103.
"Novel Binaphthalene-Amine Catalysts for the Asymmetric Epoxidation of Alkenes"
Page, P. C. B.; Farah, M. M.; Buckley, B. R.; Blacker, A. J.; Lacour, J.
Synlett2008, 1381-1385open archive unige:8458
102.
"Synthesis, Resolution, and VCD Analysis of an Enantiopure Diazaoxatricornan Derivative"
Mobian, P.; Nicolas, C.; Francotte, E.; Bürgi, T.; Lacour, J.
J. Am. Chem. Soc.2008, 130, 6507-6514open archive unige:7042 full text [restricted access]
Using simple organic synthetic transformations, a novel diazaoxatricornan derivative, the 12c-methyl-12-phenyl-8-propyl-12,12c-dihydro-8H-4-oxa-8,12-diazadibenzo[cd,mn]pyrene (6a), was prepared. This novel chiral cup-shaped molecule was isolated in racemic form and in excellent yield after the addition of methyl lithium to the BF4 salt of a novel unsymmetrical diazaoxatriangulenium cation. Compound 6a was found to be stable under classical laboratory conditions—something not obvious considering the extreme stability of the carbenium ion precursor, the electron-rich nature of the core, and the strain induced by the pyramidalization of the central carbon. The enantiomers were readily separated by chiral stationary phase chromatography, and the absolute configuration of (−)-(S)-6a was determined by a comparison of the experimental and theoretical vibrational circular dichroism (VCD) spectra. This isolation of (−)-(S)-6a and (+)-(R)-6a constitutes thus the first report of a nonracemic closed-capped chiral bowl molecule for which the chirality is due to the intrinsic dissymmetry of the central core of the structure only.
101.
"Enantioselective Olefin Epoxidation using Axially Chiral Biaryl Azepinium Salts as Catalysts. Rapid in-situ Screening and Origin of the Stereocontrol"
Novikov, R.; Bernardinelli, G.; Lacour, J.
Adv. Synth. Catal.2008, 350, 1113-1124open archive unige:7051 full text [restricted access]
100.
"Enantio- and Regioselective CpRu Catalyzed Carroll Rearrangement"
Austeri, M.; Buron, F.; Constant, S.; Lacour, J.; Linder, D.; Müller, J.; Tortoioli, S.
Pure Appl. Chem.2008, 80, 967-977open archive unige:8007 full text [restricted access]
99.
"Enantioselective [1,2]-Stevens Rearrangement of Quaternary Ammonium Salts. A Mechanistic Evaluation"
Gonçalves-Farbos, M.-H.; Vial, L.; Lacour, J.
Chem. Commun.2008, 829-831open archive unige:7
Using a supramolecular asymmetric ion pairing strategy, an enantioselective [1,2]-Stevens is feasible on substrates devoid of stereogenic quaternary nitrogen atoms.
"Tris(2,4,6-trimethoxyphenyl)methyl Carbenium Ion for Charge Derivatization of Amines and Amino Acids"
Denekamp, C.; Lacour, J.; Laleu, B.; Rabkin, E.
J. Mass Spectrom.2008, 43, 623-627open archive unige:7954 full text [restricted access]
96.
"Sugar Derived Hexacoordinated Phosphates: Chiral Anionic Auxiliaries with General Asymmetric Efficiency"
Pérollier, C.; Bernardinelli, G.; Lacour, J.
Chirality2008, 20, 313-324open archive unige:25
"Air- and Microwave-Stable (C5H5)Ru Catalysts for Improved Regio- and Enantioselective Carroll Rearrangements"
Constant, S.; Tortoioli, S.; Müller, J.; Linder, D.; Buron, F.; Lacour, J.
Angew. Chem. Int. Ed.2007, 46, 8979-8982open archive unige:6901 full text [restricted access]
[ VIP article. This study was highlighted in Synfacts. ]
94.
"C3-Symmetric Trinuclear Molybdenum Cluster Sulfides: Configurational Stability, Supramolecular Stereocontrol, and Absolute Configuration Assignment"
Frantz, R.; Guillamón, E.; Lacour, J.; Llusar, R.; Polo, V.; Vicent, C.
Inorg. Chem.2007, 46, 10717-10723open archive unige:6914 full text [restricted access]
93.
"Hexacoordinated Phosphates: How to Teach Old Chiral Anions New Asymmetric Tricks"
Lacour, J.; Linder, D.
Chem. Rec.2007, 7, 275-285open archive unige:7734 full text [restricted access]
92.
"Chiral or not chiral? A case study of the hexanuclear metalloprisms [Cp*6M6(μ3-tpt-κN)2(μ-C2O4-κO)3]6+ (M = Rh, Ir, tpt = 2,4,6-tri(pyridin-4-yl)-1,3,5-triazine)"
Govindaswamy, P.; Linder, D.; Lacour, J.; Süss-Fink, G.; Therrien, B.
Dalton Trans.2007, 4457-4463open archive unige:6661 full text [free access]
"Bimetallic Iridium(III) Complexes Consisting of Ir(ppy)2 Units (ppy = 2-Phenylpyridine) and Two Laterally Connected N^N Chelates as Bridge: Synthesis, Separation, and Photophysical Properties Bimetallic Iridium(III) Complexes consistin"
Auffrant, A.; Barbieri, A.; Barigelletti, F.; Lacour, J.; Mobian, P.; Collin, J.-P.; Sauvage, J.-P.; Ventura, B.
Inorg. Chem.2007, 46, 6911-6919open archive unige:6912 full text [restricted access]
89.
"Chiral Concave Imidazolinium Salts as Precursors to Chiral Concave N-Heterocyclic Carbenes"
Winkelmann, O.; Linder, D.; Lacour, J.; Näther, C.; Lüning, U.
Eur. J. Org. Chem.2007, 3687-3697open archive unige:7746 full text [restricted access]
88.
"Enantioselective olefin epoxidation using novel doubly bridged biphenyl azepines as catalysts"
Novikov, R.; Vachon, J.; Lacour, J.
Chimia2007, 61, 236-239open archive unige:7738 full text [restricted access]
87.
"TRISPHAT-N: A Chiral Hexacoordinated Phosphate Anion with Unique Asymmetric Coordinating Properties"
Constant, S.; Frantz, R.; Müller, J.; Bernardinelli, G.; Lacour, J.
Organometallics2007, 26, 2141-2143open archive unige:6934 full text [restricted access]
86.
"Enantiodifferentiation of chiral cationic cages using trapped achiral BF4- anions as chirotopic probes"
Frantz, R.; Grange, C. S.; Al-Rasbi, N. K.; Ward, M. D.; Lacour, J.
Chem. Commun.2007, 1459-1461open archive unige:6905 full text [restricted access]
"Effective HPLC resolution of [4]heterohelicenium dyes on chiral stationary phases using reversed phase eluents"
Villani, C.; Laleu, B.; Mobian, P.; Lacour, J.
Chirality2007, 19, 601-606open archive unige:7741 full text [restricted access]
81.
"Unusual packing of ET molecules caused by π-π stacking interactions with TRISPHAT molecules in two [ET][TRISPHAT] salts (ET = bis(ethylenedithio)tetrathiafulvalene, TRISPHAT = (tris(tetrachlorobenzenediolato)phosphate(V)))"
Clemente-León, M.; Coronado, E.; Gómez-García, C. J.; Soriano-Portillo, A.; Constant, S.; Frantz, R.; Lacour, J.
Inorg. Chim. Acta2007, 360, 955-960open archive unige:7056 full text [restricted access]
"Enantioselective olefin epoxidation using novel biphenyl and binaphthyl azepines and azepinium salts"
Vachon, J.; Lauper, C.; Ditrich, K.; Lacour, J.
Tetrahedron: Asymmetry2006, 17, 2334-2338open archive unige:7058 full text [restricted access]
79.
"Self-assembled hexanuclear arene ruthenium metallo-prisms with unexpected double helical chirality"
Govindaswamy, P.; Linder, D.; Lacour, J.; Süss-Fink, G.; Therrien, B.
Chem. Commun.2006, 4691-4693open archive unige:6908 full text [restricted access]
78.
"Triazatriangulenium Cations: Highly Stable Carbocations for Phase-Transfer Catalysis"
Nicolas, C.; Lacour, J.
Org. Lett.2006, 8, 4343-4346open archive unige:6932 full text [restricted access]
77.
"Trimesitylmethylphosphonium Cation. Supramolecular Stereocontrol and Simple Enantiomerization Mechanism Determination"
Laleu, B.; Bernardinelli, G.; Chauvin, R.; Lacour, J.
J. Org. Chem.2006, 71, 7412-7416open archive unige:6916 full text [restricted access]
76.
"Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison"
Gonçalves, M.-H.; Martinez, A.; Grass, S.; Page, P. C. B.; Lacour, J.
Tetrahedron Lett.2006, 47, 5297-5301open archive unige:7059 full text [restricted access]
75.
"Pummerer fragmentation vs. Pummerer rearrangement: a mechanistic analysis"
Laleu, B.; Machado, M. S.; Lacour, J.
Chem. Commun.2006, 2786-2788open archive unige:6907 full text [restricted access]
74.
"Recent developments in enantioselective phase transfer catalysis using chiral ammonium salts"
Vachon, J.; Lacour, J.
Chimia2006, 60, 266-275open archive unige:7735 full text [restricted access]
73.
"Effective chiral recognition among ions in polar medium"
Bergman, S. D.; Frantz, R.; Gut, D.; Kol, M.; Lacour, J.
Chem. Commun.2006, 850-852open archive unige:6909 full text [restricted access]
72.
"Chiral Spiro Cu(I) Complexes. Supramolecular Stereocontrol and Isomerisation Dynamics by Use of TRISPHAT Anions"
Hebbe-Viton, V.; Desvergnes, V.; Jodry, J. J.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J.
Dalton Trans.2006, 2058-2065open archive unige:6662 full text [free access]
"Towards the stereoselective synthesis of inherently chiral pseudorotaxanes"
Mobian, P.; Banerji, N.; Bernardinelli, G.; Lacour, J.
Org. Biomol. Chem.2006, 4, 224-231open archive unige:6926 full text [restricted access]
70.
"Ion-Pairing Effects in the Self-Assembly of a Fluorescent Pseudorotaxane"
Clemente-León, M.; Pasquini, C.; Hebbe-Viton, V.; Lacour, J.; Dalla Cort, A.; Credi, A.
Eur. J. Org. Chem.2006, 105-112open archive unige:7745 full text [restricted access]
"Biphasic Enantioselective Olefin Epoxidation Using Tropos Dibenzoazepinium Catalysts"
Vachon, J.; Pérollier, C.; Monchaud, D.; Marsol, C.; Ditrich, K.; Lacour, J.
J. Org. Chem.2005, 70, 5903-5911open archive unige:6951 full text [restricted access]
67.
"Fluorinated TRISPHAT Anions: Spectroscopic Probes for Detailed Asymmetric Ion Pairing Studies"
Frantz, R.; Pinto, A.; Constant, S.; Bernardinelli, G.; Lacour, J.
Angew. Chem. Int. Ed.2005, 44, 5060-5064open archive unige:6981 full text [restricted access]
66.
"Matched/Mismatched Interaction of a Cyclic Hexapeptide with Ion Pairs Containing Chiral Cations and Chiral Anions"
Heinrichs, G.; Kubik, S.; Lacour, J.; Vial, L.
J. Org. Chem.2005, 70, 4498-4501open archive unige:6950 full text [restricted access]
65.
"Resolution of [4]Heterohelicenium Dyes via Unprecedented Pummerer-like Chemistry"
Laleu, B.; Mobian, P.; Herse, C.; Laursen, B. W.; Hopfgartner, G.; Bernardinelli, G.; Lacour, J.
Angew. Chem. Int. Ed.2005, 44, 1879-1883open archive unige:2389 full text [restricted access]
"Large-Scale Synthesis and Resolution of TRISPHAT [Tris(tetrachlorobenzenediolato) phosphate(V)] Anion"
Favarger, F.; Goujon-Ginglinger, C.; Monchaud, D.; Lacour, J.
J. Org. Chem.2004, 69, 8521-8524open archive unige:6949 full text [restricted access]
60.
"Synthesis and Stereochemical Properties of Chiral Square Complexes of Iron(II)"
Bark, T.; von Zelewsky, A.; Rappoport, D.; Neuburger, M.; Schaffner, S.; Lacour, J.; Jodry, J. J.
Chem. Eur. J.2004, 10, 4839-4845open archive unige:7762 full text [restricted access]
59.
"Syntheses of Nonracemic Ortho-Mercurated and Ortho-Ruthenated Complexes of 2-[Tricarbonyl(η6-phenyl)chromium]pyridine"
Djukic, J.-P.; Berger, A.; Pfeffer, M.; de Cian, A.; Kyritsakas-Gruber, N.; Vachon, J.; Lacour, J.
Organometallics2004, 23, 5757-5767open archive unige:6945 full text [restricted access]
58.
"Unusual Regio- and Enantioselective [1,2]-Stevens Rearrangement of a Spirobi[dibenzazepinium] Cation"
Vial, L.; Gonçalves, M.-H.; Morgantini, P.-Y.; Weber, J.; Bernardinelli, G.; Lacour, J.
Synlett2004, 1565-1568open archive unige:3256
57.
"Chiral Induction in a Ribose-Decorated Metallostar through Intrinsic and Interionic Diastereomeric Interactions"
Constable, E. C.; Frantz, R.; Housecroft, C. E.; Lacour, J.; Mahmood, A.
Inorg. Chem.2004, 43, 4817-4819open archive unige:7019 full text [restricted access]
56.
"Supramolecular Stereocontrol of Octahedral Metal-Centered Chirality. Ligand Modulation"
Jodry, J. J.; Frantz, R.; Lacour, J.
Inorg. Chem.2004, 43, 3329-3331open archive unige:7018 full text [restricted access]
55.
"1H, 19F and 31P PGSE NMR Diffusion Studies on Chiral Organic Salts: Ion Pairing and the Dependence of a Diffusion Value on Diastereomeric Structure"
Martínez-Viviente, E.; Pregosin, P. S.; Vial, L.; Herse, C.; Lacour, J.
Chem. Eur. J.2004, 10, 2912-2918open archive unige:7761 full text [restricted access]
"Chloride-Promoted Synthesis of Cis Bis-Chelated Palladium(II) Complexes from Ortho-Mercurated Tricarbonyl(η6-arene)chromium Complexes"
Berger, A.; Djukic, J.-P.; Pfeffer, M.; Lacour, J.; Vial, L.; de Cian, A.; Kyritsakas-Gruber, N.
Organometallics2003, 22, 5243-5260open archive unige:6942 full text [restricted access]
53.
"Mannose Derived Hexacoordinated Phosphate–a Generally Efficient Chiral Anion for Asymmetric Applications"
Pérollier, C.; Constant, S.; Jodry, J. J.; Bernardinelli, G.; Lacour, J.
Chem. Commun.2003, 2014-2015open archive unige:6964 full text [restricted access]
52.
"Bent Structure and Dynamic Stereochemistry of Chiral Acridinium Cations"
Laleu, B.; Herse, C.; Laursen, B. W.; Bernardinelli, G.; Lacour, J.
J. Org. Chem.2003, 68, 6304-6308open archive unige:6948 full text [restricted access]
51.
"A Highly Configurationally Stable [4]Heterohelicenium Cation"
Herse, C.; Bas, D.; Krebs, F. C.; Bürgi, T.; Weber, J.; Wesolowski, T.; Laursen, B. W.; Lacour, J.
Angew. Chem. Int. Ed.2003, 42, 3162-3166open archive unige:3238 full text [free access]
"Enantioselective Recognition of a Chiral Quaternary Ammonium Ion by C3 Symmetric Cyclic Hexapeptides"
Heinrichs, G.; Vial, L.; Lacour, J.; Kubik, S.
Chem. Commun.2003, 1252-1253open archive unige:6963 full text [restricted access]
48.
"Chiral Anion Mediated Asymmetric Chemistry: Advantages and Perspectives"
Lacour, J.
Chimia2003, 57, 168open archive unige:7790 full text [restricted access]
47.
"NMR Enantiodifferentiation of Triphenylphosphonium Salts by Chiral Hexacoordinated Phosphate Anions"
Hebbe, V.; Londez, A.; Goujon-Ginglinger, C.; Meyer, F.; Uziel, J.; Jugé, S.; Lacour, J.
Tetrahedron Lett.2003, 44, 2467-2471open archive unige:7009 full text [restricted access]
46.
"Novel Heteroleptic cis-(C^N2)Pd(II) Chelates for the Preparation of Enantiopure Planar Chiral Cyclopalladated 2-[tricarbonyl(η6-phenyl)chromium]pyridine"
Berger, A.; Djukic, J.-P.; Pfeffer, M.; de Cian, A.; Kyritsakas-Gruber, N.; Lacour, J.; Vial, L.
Chem. Commun.2003, 658-659open archive unige:6966 full text [restricted access]
45.
"Comparison of the NMR Enantiodifferentiation of a Chiral Ruthenium(II) Complex of C2 Symmetry Using the TRISPHAT Anion and a Lanthanide Shift Reagent"
Bruylants, G.; Bresson, C.; Boisdenghien, A.; Pierard, F.; Kirsch-De Mesmaeker, A.; Lacour, J.; Bartik, K.
New J. Chem.2003, 27, 748-751open archive unige:7022 full text [restricted access]
44.
"Synthesis, Enantiomeric Conformations, and Stereodynamics of Aromatic ortho-Substituted Disulfones"
Lacour, J.; Monchaud, D.; Mareda, J.; Favarger, F.; Bernardinelli, G.
Helv. Chim. Acta2003, 86, 65-81open archive unige:7832 full text [restricted access]
43.
"NMR Evaluation of the Configurational Stability of Cu(I) Complexes"
Desvergnes-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J.
Inorg. Chem.2003, 42, 255-257open archive unige:7016 full text [restricted access]
"Conformational Preference and Configurational Control of Highly Symmetric Spirobi[dibenzazepinium] Cation"
Vial, L.; Lacour, J.
Org. Lett.2002, 4, 3939-3942open archive unige:6959 full text [restricted access]
"One-Step Stereoselective Synthesis and NMR Chiral Shift Properties of a Novel Hexacoordinated Phosphorus Cation"
Lacour, J.; Vial, L.; Bernardinelli, G.
Org. Lett.2002, 4, 2309-2312open archive unige:6958 full text [restricted access]
"Crystal Packing Interpretation of the Association of Chiral Threefold Propellor Ions: Trisphat Anion With a Triarylcarbenium Cation"
Lacour, J.; Bernardinelli, G.; Russell, V.; Dance, I.
CrystEngComm2002, 4, 165-170open archive unige:7915 full text [restricted access]
35.
"Ion-Pair Mediated Asymmetric Synthesis of a Configurationally Stable Mononuclear Tris(diimine) Iron(II) Complex"
Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J.
Angew. Chem. Int. Ed.2002, 41, 2317-2319open archive unige:6975 full text [restricted access]
"Chiral Anion Mediated Asymmetric Induction onto Chiral Diquats"
Pasquini, C.; Desvergnes-Breuil, V.; Jodry, J. J.; Dalla Cort, A.; Lacour, J.
Tetrahedron Lett.2002, 43, 423-426open archive unige:7008 full text [restricted access]
31.
"Diastereoselective Synthesis of C2-symmetric Hexacoordinated Phosphate Anions (HYPHATs) with Predetermined Chirality from 1,2-Diaryl-ethane-1,2-diols"
Lacour, J.; Londez, A.
J. Organomet. Chem.2002, 643-644, 392-403open archive unige:7759 full text [restricted access]
"Configurational Ordering of a Cationic Dinuclear Triple Helicate by Chiral TRISPHAT Anions"
Lacour, J.; Jodry, J. J.; Monchaud, D.
Chem. Commun.2001, 2302-2303open archive unige:7802 full text [restricted access]
29.
"TRISPHAT Anion. An Efficient NMR Chiral Shift Counterion for Cationic Tricarbonyl Manganese Complexes with Planar Chirality"
Giner Planas, J.; Prim, D.; Rose, E.; Rose-Munch, F.; Monchaud, D.; Lacour, J.
Organometallics2001, 20, 4107-4110open archive unige:6939 full text [restricted access]
28.
"Synthesis, Enantiomeric Conformations, and Stereodynamics of Aromatic ortho-Substituted Disulfones"
Monchaud, D.; Lacour, J.; Bernardinelli, G.; Favarger, F.
Org. Lett.2001, 3, 1407-1410open archive unige:6957 full text [restricted access]
27.
"TRISPHAT Salts. Efficient NMR Chiral Shift and Resolving Agents for Substituted Cyclometallated Ruthenium Bis(diimine) Complexes"
Monchaud, D.; Lacour, J.; Coudret, C.; Fraysse, S.
J. Organomet. Chem.2001, 624, 388-391open archive unige:7758 full text [restricted access]
"Efficient Resolution of Dinuclear Triple Helicate By Asymmetric Extraction/Precipitation Using TRISPHAT Anions as Resolving Agents"
Jodry, J. J.; Lacour, J.
Chem. Eur. J.2000, 6, 4297-4304open archive unige:7767 full text [restricted access]
23.
"[n-Bu4N][Δ-TRISPHAT] Salt. Efficient NMR Chiral Shift Reagent for Neutral Planar Chiral Tricarbonyl Chromium Complexes"
Ratni, H.; Jodry, J. J.; Lacour, J.; Kündig, E. P.
Organometallics2000, 19, 3997-3999open archive unige:6938 full text [restricted access]
22.
"Efficient Enantioselective Extraction of Ruthenium(II) Tris(diimine) Complexes by Chiral Lipophilic TRISPHAT Anions"
Lacour, J.; Goujon-Ginglinger, C.; Torche-Haldimann, S.; Jodry, J. J.
Angew. Chem. Int. Ed.2000, 39, 3695-3697open archive unige:7815 full text [restricted access]
"1H and 31P NMR Determination of the Enantiomeric Purity of Quaternary Phosphonium Cations Using TRISPHAT as Chiral Shift Agent"
Ginglinger, C.; Jeannerat, D.; Lacour, J.; Jugé, S.; Uziel, J.
Tetrahedron Lett.1998, 39, 7495-7498open archive unige:7003 full text [restricted access]
19.
"Diastereoselektive Ionenpaarbildung des TRISPHAT-Anions mit Tris(4,4'-dimethyl-2,2'-bipyridin)eisen(II)"
Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S.
Angew. Chem.1998, 110, 2522-2524open archive unige:7807 full text [restricted access]
18.
"Ion Pair Chromatographic Resolution of Tri(diimine)ruthenium(II) Complexes Using TRISPHAT Anions as Resolving Agents"
Lacour, J.; Torche-Haldimann, S.; Jodry, J. J.; Ginglinger, C.; Favarger, F.
Chem. Commun.1998, 1733-1734open archive unige:7801 full text [restricted access]
17.
"Asymmetric Recognition of TRISPHAT Anion. Unusually High Difference in Reactivity of the Pseudoenantiomers of Cinchona Alkaloids"
Lacour, J.; Ginglinger, C.; Favarger, F.
Tetrahedron Lett.1998, 39, 4825-4828open archive unige:7001 full text [restricted access]
16.
"Simple Ion Exchange Procedure of Common Anions to TRISPHAT. Application to the Purification of Cationic Species"
Lacour, J.; Barchéchath, S.; Jodry, J. J.; Ginglinger, C.
Tetrahedron Lett.1998, 39, 567-570open archive unige:7004 full text [restricted access]
"32nd Euchem Stereochemistry Conference, Bürgenstock, April 27- May 3, 1997"
de Brabander, J.; Lacour, J.
Chimia1997, 51, 657
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14.
"Application of TRISPHAT Anion as NMR Chiral Shift Reagent"
Lacour, J.; Ginglinger, C.; Favarger, F.; Torche-Haldimann, S.
Chem. Commun.1997, 2285-2286open archive unige:7800 full text [restricted access]
13.
"Synthese und Trennung der Enantiomere des konfigurationsstabilen Tris(tetrachlorbenzoldiolato)phosphat(V)-Ions"
Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G.
Angew. Chem.1997, 109, 660-662open archive unige:6973 full text [restricted access]
12.
"Approaches to the Synthesis of the Vancomycin antibiotics. Synthesis of Orienticin C (Bis-dechlorovancomycin) Aglycon"
Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J.
J. Am. Chem. Soc.1997, 119, 3419-3420open archive unige:7855 full text [restricted access]
11.
"Applications of the β-Azidonation Reaction to Organic Synthesis. α,β-Enones, Conjugate Addition, and γ-Lactam Annulation"
Magnus, P.; Lacour, J.; Evans, P. A.; Rigollier, P.; Tobler, H.
J. Am. Chem. Soc.1998, 120, 12486-12499open archive unige:7858 full text [restricted access]
10.
"N-Methyl Azidonation of N,N-Dimethylarylamines with the Iodosylbenzene/Trimethylsilylazide Reagent Combination and some Reactions of α-Azidomethylamines"
Magnus, P.; Lacour, J.; Weber, W.
Synthesis1998, 547-551
"Hypervalent Iodine Chemistry: New Oxidation Reactions Using the Iodosylbenzene-Trimethylsilyl Azide Reagent Combination. Direct α- and β-Azido Functionalization of Triisopropylsilyl Enol Ethers"
Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C.
J. Am. Chem. Soc.1996, 118, 3406-3418open archive unige:7852 full text [restricted access]
"New Trialkylsilyl Enol Ether Chemistry: α-N-Tosylamination of Triisopropylsilyl Enol Ethers"
Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B.
Tetrahedron1995, 51, 11087-11110open archive unige:7806 full text [restricted access]
"New Trialkylsilyl Enol Ether Chemistry: Intramolecular [2 + 2] Cyclizations of β-Amido Triisopropylsilyl Enol Ethers"
Magnus, P.; Rigollier, P.; Lacour, J.; Tobler, H.
J. Am. Chem. Soc.1993, 115, 12629-12630open archive unige:7850 full text [restricted access]
6.
"Direct N-Alkyl Azidonation of N,N-dialkylarylamines with the Iodosylbenzene/Trimethyl-silylazide Reagent Combination"
Magnus, P.; Lacour, J.; Weber, W.
J. Am. Chem. Soc.1993, 115, 9347-9348open archive unige:7849 full text [restricted access]
5.
"New Trialkylsilyl Enol Ether Chemistry"
Magnus, P.; Lacour, J.; Evans, A.
Janssen Chimica Acta1993, 11, 3-7
open archive unige:6249
"New Trialkylsilyl Enol Ether Chemistry: New Regiospecific Methodology for the Synthesis of α,β-Unsaturated Cyclic Ketones"
Magnus, P.; Evans, A.; Lacour, J.
Tetrahedron Lett.1992, 33, 2933-2936open archive unige:6608
full text
CH2).
