Diastereoselection in the conjugate additions of organocopper reagents to N-enoyloxazolidinones

A survey of conjugate additions of Yamamoto organocopper reagents to N-enoyl-4-substituted oxazolidinones is reported. Diastereofacial selectivity is reversed for 4-phenyl and 4-benzyloxazolidinones of the same relative configuration. Alkenylcopper reagents demonstrate superior results in asymmetric...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 47; pp. 8593 - 8596
Main Authors Williams, David R, Kissel, William S, Li, Jie Jack
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.11.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,4-ADDITION
ACIDS
DERIVATIVES
UNSATURATED CHIRAL IMIDES
ENOATES
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Summary:A survey of conjugate additions of Yamamoto organocopper reagents to N-enoyl-4-substituted oxazolidinones is reported. Diastereofacial selectivity is reversed for 4-phenyl and 4-benzyloxazolidinones of the same relative configuration. Alkenylcopper reagents demonstrate superior results in asymmetric additions using the 4-phenyloxazolidinone auxiliary. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01966-2