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

Show more

Author(s)

Murray, James I

Flodén, Nils J

Bauer, Adriano

Fessner, Nico D

Dunklemann, Daniel L

more

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.

Show more

Date Issued

2017-05-15

Date Acceptance

2017-03-28

Citation

Angewandte Chemie, 2017, 129 (21), pp.5854-5858

URI

http://hdl.handle.net/10044/1/64867

DOI

https://www.dx.doi.org/10.1002/ange.201700977

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