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Publication 96  

  1. Sugar Derived Hexacoordinated Phosphates: Chiral Anionic Auxiliaries with General Asymmetric Efficiency
    Céline Pérollier, Gérald Bernardinelli, Jérôme Lacour
    Chirality 2008, 20, 313-324

Mannose-derived hexacoordinated phosphate anions, prepared in as few as two steps from methyl-α-d-mannopyranoside and tris(dimethylamino)phosphine, are chiral anionic auxiliaries with broad asymmetric efficiency. These chemically robust anions are effective NMR chiral solvating agents and efficient asymmetry-inducers, able to control the configuration of conformationally labile C2-symmetric monomethinium cations (organic, helical, charge 1+, P or M enantiomers) and D3-symmetric iron(II) trisdiimine complexes (metallo-organic, octahedral, charge 2+, Δ or Λ enantiomers). Diastereomeric control with often unmatched selective levels was achieved with the help of mannopyranoside backbone of the anions and the substituents on the [1,3]dioxane ring that play a key role in the recognition process, something not obvious at first sight.

DOI: 10.1002/chir.20441 

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