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HERO ID
7442450
Reference Type
Journal Article
Title
KINETIC RESOLUTION OF BETA-STEREOGENIC O-ALKYL CARBAMATES BY (-)-SPARTEINE-ASSISTED DEPROTONATION - EXTERNAL VERSUS INTERNAL CHIRAL INDUCTION
Author(s)
Haller, J; Hense, T; Hoppe, D
Year
1993
Is Peer Reviewed?
1
Journal
Synlett
ISSN:
0936-5214
EISSN:
1437-2096
Publisher
Georg Thieme Verlag
Volume
1993
Issue
10
Page Numbers
726-728
Language
English
DOI
10.1055/s-1993-22585
Web of Science Id
WOS:A1993MC14700003
URL
http://www.thieme-connect.de/DOI/DOI?10.1055/s-1993-22585
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Abstract
The chiral base s-butyllithium/(-)-sparteine recognizes the (ft)-enantiomer in a 2-phenylpropyl carbamate and the (5)-enantiomer in a l-(l,2,3,4-tetrahydronaphthyl)methyl carbamate. In addition with its high preference for the pro-5-proton, highly diastereoselective electrophilic substitutions in the o-position of R-phenylalkanols, combined with efficient kinetic resolution of the ra-cemate, are achieved. © 1993 Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved.
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