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Scientific article
English

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst

Published inAngewandte Chemie, vol. 56, no. 21, p. 5760-5764
Publication date2017
Abstract

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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Citation (ISO format)
MURRAY, James I. et al. Kinetic Resolution of 2-Substituted Indolines by <i>N</i>-Sulfonylation using an Atropisomeric 4-DMAP-<i>N</i>-oxide Organocatalyst. In: Angewandte Chemie, 2017, vol. 56, n° 21, p. 5760–5764. doi: 10.1002/anie.201700977
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ISSN of the journal1433-7851
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Creation05/10/2017 10:41:00 AM
First validation05/10/2017 10:41:00 AM
Update time03/15/2023 1:39:43 AM
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