Stereoselective synthesis of racemic α-amino-acid derivatives with a β-lactam skeleton: Application of the Staudinger reaction to chiral imines of methyl glyoxylate

Selected imines of methyl glyoxylate act as good partners in the Staudinger cycloaddition reaction with a series of substituted ketenes. The cis stereoselectivity is almost complete with electron-donor substituted ketenes, but the asymmetric induction is low when imines derived from chiral 1-aryl-et...

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Bibliographic Details
Published inTetrahedron Vol. 54; no. 38; pp. 11501 - 11516
Main Authors Barreau, Michel, Commerçon, Alain, Mignani, Serge, Mouysset, Dominique, Perfetti, Patricia, Stella, Lucien
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.09.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BIOACTIVE CONFORMATION
CYCLOADDITION
DESIGN
PEPTIDOMIMETICS
ANTIBIOTICS
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
N-DEARYLATION
DIELS-ALDER REACTION
ESTER-DERIVED IMINES
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Summary:Selected imines of methyl glyoxylate act as good partners in the Staudinger cycloaddition reaction with a series of substituted ketenes. The cis stereoselectivity is almost complete with electron-donor substituted ketenes, but the asymmetric induction is low when imines derived from chiral 1-aryl-ethylamines are used. Complete cis stereoselectivity, but low asymmetric induction are observed when imines derived from chiral 1-arylethylamines are used
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00683-8