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Kinetic Resolution of 2‐Substituted Indolines by N ‐Sulfonylation using an Atropisomeric 4‐DMAP‐ N ‐oxide Organocatalyst
Author(s) -
Murray James I.,
Flodén Nils J.,
Bauer Adriano,
Fessner Nico D.,
Dunklemann Daniel L.,
BobEgbe Opetoritse,
Rzepa Henry S.,
Bürgi Thomas,
Richardson Jeffery,
Spivey Alan C.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700977
Subject(s) - chemistry , kinetic resolution , isopropyl , sulfonamide , chloride , catalysis , oxide , organic chemistry , thioglycolic acid , medicinal chemistry , combinatorial chemistry , enantioselective synthesis
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.