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Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with ?,?-unsaturated aldehydes.

ABSTRACT: LUMO-lowering organocatalysis has been extended to promote the conjugate addition of S-alkyl and -pyrrolyl silylketene acetals to ?,?-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.

SUBMITTER: Borths CJ

PROVIDER: S-EPMC4158731 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes.

Borths Christopher J CJ Carrera Diane E DE MacMillan David W C DW

Tetrahedron 20090801 33

LUMO-lowering organocatalysis has been extended to promote the conjugate addition of S-alkyl and -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. ...[more]

PMID: 25214677

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