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

Christopher J Borths; Diane E Carrera; David W C MacMillan

doi:10.1016/j.tet.2009.06.066

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

Tetrahedron. 2009 Aug 15;65(33):6746-6753. doi: 10.1016/j.tet.2009.06.066.

Authors

Christopher J Borths¹, Diane E Carrera¹, David W C MacMillan¹

Affiliation

¹ Merck Center for Catalysis, Princeton University, Princeton, NJ 08544, United States ; The Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, United States.

Abstract

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.

Keywords: Mukaiyama–Michael; nantioselective organocatalysis.

Grants and funding

R01 GM078201/GM/NIGMS NIH HHS/United States