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 Dunkelmann Opetoritse Bob-Egbe Henry S Rzepa Thomas Buergi Jeffery Richardson Alan C Spivey

Published in: Angewandte Chemie (International ed. in English) (2017)

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.

Keyphrases

molecular docking
single molecule
quantum dots
oxide nanoparticles
metal organic framework