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 inTetrahedron Vol. 65; no. 33; pp. 6746 - 6753
Main Authors Borths, Christopher J., Carrera, Diane E., MacMillan, David W.C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.08.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Enantioselective organocatalysis
Mukaiyama–Michael
Physical Sciences
Science & Technology
Mukaiyama–Michael
Enantioselective organocatalysis
CATALYZED ASYMMETRIC 1,4-ADDITION
CHIRAL LEWIS-ACIDS
KETONES
Mukaiyama-Michael
SILYL ENOL ETHERS
ADDITIONS
DERIVATIVES
BIS(OXAZOLINE) COPPER(II) COMPLEXES
SILYLKETENE ACETALS
nantioselective organocatalysis
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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. [Display omitted]
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
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ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.06.066