Development of a general, enantioselective organocatalytic Mukaiyama–Michael reaction with α,β-unsaturated aldehydes
LUMO-lowering organocatalysis has been extended to promote the conjugate addition of S-alkyl and 1-pyrrolyl silylketene acetals to α,β-unsaturated aldehydes, yielding both, syn and anti Mukaiyama–Michael products with high levels of enantioselectivity. This strategy allows for the generation of chem...
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Published in | Tetrahedron Vol. 65; no. 33; pp. 6746 - 6753 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
15.08.2009
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | LUMO-lowering organocatalysis has been extended to promote the conjugate addition of
S-alkyl and 1-pyrrolyl silylketene acetals to α,β-unsaturated aldehydes, yielding both,
syn and
anti Mukaiyama–Michael products with high levels of enantioselectivity. This strategy allows for the generation of chemically useful 1,5-dicarbonyl systems and again highlights the utility of organocatalysis.
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Bibliography: | Medline NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2009.06.066 |