Kinetic Resolution of 2-Substituted Indolines by N -Sulfonylation using an Atropisomeric 4-DMAP- N -oxide Organocatalyst
File(s)Sulfonylative KR Angew FINAL REVISED.pdf (1.1 MB)
Accepted version
Author(s)
Type
Journal Article
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.
Date Issued
2017-05-15
Date Acceptance
2017-03-28
Citation
Angewandte Chemie, 2017, 129 (21), pp.5854-5858
ISSN
0044-8249
Publisher
Wiley-VCH Verlag GmbH
Start Page
5854
End Page
5858
Journal / Book Title
Angewandte Chemie
Volume
129
Issue
21
Copyright Statement
© 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: J. I. Murray, N. J. Flodén, A. Bauer, N. D. Fessner, D. L. Dunklemann, O. Bob-Egbe, H. S. Rzepa, T. Bürgi, J. Richardson, A. C. Spivey, Angew. Chem. 2017, 129, 5854., which has been published in final form at https://dx.doi.org/10.1002/ange.201700977
Subjects
03 Chemical Sciences
Organic Chemistry
Publication Status
Published
Date Publish Online
2017-04-26