• Kinetic Resolution of 2-Substituted Indolines by N -Sulfonylation using an Atropisomeric 4-DMAP- N -oxide Organocatalyst
    James I. Murray, Nils J. Flodén, Adriano Bauer, Nico D. Fessner, Daniel L. Dunklemann, Opetoritse Bob-Egbe, Henry S. Rzepa, Thomas Bürgi, Jeffery Richardson and Alan C. Spivey
    Angewandte Chemie International Edition, 56 (21) , 2017, p5760-5764
    Keywords: asymmetric catalysis;indoline;kinetic resolution;organocatalysis;sulfonylation
    DOI:10.1002/anie.201700977 | unige:94104 | Abstract | Article HTML | Article PDF | Supporting Info
 
The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.

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Bauer, Adriano Bob-Egbe, Opetoritse Bürgi, Thomas Dunklemann, Daniel L. Fessner, Nico D. 
Flodén, Nils J. Murray, James I. Richardson, Jeffery Rzepa, Henry S. Spivey, Alan C. 
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