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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Published in | Tetrahedron Vol. 54; no. 38; pp. 11501 - 11516 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
17.09.1998
Elsevier |
Subjects | |
Online Access | Get full text |
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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 |
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/S0040-4020(98)00683-8 |