Kinetic resolution of 2-substituted indolines by N-sulfonylation using an atropisomeric 4-DMAP-N-oxide organocatalyst
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Accepted version
Supporting information
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
2017-04-26
Date Acceptance
2017-03-27
Citation
Angewandte Chemie International Edition, 2017, 56 (21), pp.5760-5764
ISSN
1433-7851
Publisher
Wiley-VCH Verlag GmbH
Start Page
5760
End Page
5764
Journal / Book Title
Angewandte Chemie International Edition
Volume
56
Issue
21
Copyright Statement
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article, which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/anie.201700977/abstract
Sponsor
The Leverhulme Trust
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000400755800017&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Grant Number
F/07 058/O
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
asymmetric catalysis
indoline
kinetic resolution
organocatalysis
sulfonylation
NONENZYMATIC ACYLATION CATALYST
SOLID-PHASE SYNTHESIS
ASYMMETRIC HYDROGENATION
SECONDARY-AMINES
SELECTIVE PHOSPHORYLATION
CARBOXYLIC-ACID
LEWIS-BASE
EFFICIENT
ALCOHOLS
COMMUNICATION
Publication Status
Published
Date Publish Online
2017-04-26