Chiral Relay Effect: 4-Substituted 1,3-Benzoxazol-2-(3H)-ones as Achiral Templates for Enantioselective Diels−Alder Reactions
A new strategy to control the enantioselectivity of Lewis acid catalyzed reactions has been investigated. The use of N-acryloyl-1,3-benzoxazol-2-(3H)-ones substituted at position 4 leads to the formation of diastereomeric complexes as a result of the presence of a chiral axis. The stereochemical out...
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Published in | Organic letters Vol. 4; no. 1; pp. 39 - 42 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
10.01.2002
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | A new strategy to control the enantioselectivity of Lewis acid catalyzed reactions has been investigated. The use of N-acryloyl-1,3-benzoxazol-2-(3H)-ones substituted at position 4 leads to the formation of diastereomeric complexes as a result of the presence of a chiral axis. The stereochemical outcome of the reaction is controlled by the chiral catalyst and by the chiral axis, leading to high enantioselectivity improvements and, in one case, to an inversion of enantioselectivity. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol016966c |