title: Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes.
abstract: LUMO-lowering organocatalysis has been extended to promote the conjugate addition ofS-alkyl and -pyrrolyl silylketene acetals to α,β-unsaturated aldehydes, yielding both,synandantiMukaiyama-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.
authors.affiliation: 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.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Borths
authors.affiliation: 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.
authors.forename: Diane E
authors.initials: DE
authors.lastname: Carrera
authors.affiliation: 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.
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
keywords: Mukaiyama–Michael; nantioselective organocatalysis