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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Bibliographic Details
Published inOrganic letters Vol. 4; no. 1; pp. 39 - 42
Main Authors Quaranta, Laura, Corminboeuf, Olivier, Renaud, Philippe
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.01.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
COPPER(II) COMPLEXES
LEWIS-ACID CATALYSTS
ASYMMETRIC INDUCTION
ENANTIOMERS
TRIFLATE CATALYSTS
BIS(OXAZOLINE)-MAGNESIUM
BIS(OXAZOLINE)COPPER(II) COMPLEXES
ALPHA-AMINO-ACIDS
ALDOL REACTIONS
AUXILIARY
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol016966c