Catalytic Michael reactions of ketoesters with a camphor-derived acrylate equivalent: stereoselective access to all-carbon quaternary centers

Claudio Palomo; Mikel Oiarbide; Jesús M García; Patricia Bañuelos; José M Odriozola; Jesús Razkin; Anthony Linden

doi:10.1021/ol800564d

Catalytic Michael reactions of ketoesters with a camphor-derived acrylate equivalent: stereoselective access to all-carbon quaternary centers

Org Lett. 2008 Jul 3;10(13):2637-40. doi: 10.1021/ol800564d. Epub 2008 Jun 3.

Authors

Claudio Palomo¹, Mikel Oiarbide, Jesús M García, Patricia Bañuelos, José M Odriozola, Jesús Razkin, Anthony Linden

Affiliation

¹ Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain. claudio.palomo@ehu.es

PMID: 18517215
DOI: 10.1021/ol800564d

Abstract

A camphor-based alpha'-hydroxy enone reagent acts as a chiral acrylate equivalent in copper-catalyzed Michael reactions of beta-keto esters and affords products that possess all-carbon quaternary stereocenters of high enantiomeric purity.