Copper-catalyzed enantioselective 1,4-addition to alpha,beta-unsaturated aldehydes

Laëtitia Palais; Lucille Babel; Adrien Quintard; Sébastien Belot; Alexandre Alexakis

doi:10.1021/ol100441r

Copper-catalyzed enantioselective 1,4-addition to alpha,beta-unsaturated aldehydes

Org Lett. 2010 May 7;12(9):1988-91. doi: 10.1021/ol100441r.

Authors

Laëtitia Palais¹, Lucille Babel, Adrien Quintard, Sébastien Belot, Alexandre Alexakis

Affiliation

¹ Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Geneve, Switzerland.

PMID: 20359170
DOI: 10.1021/ol100441r

Abstract

The first asymmetric Cu-catalyzed conjugate addition of dialkylzinc zinc reagents to a large scope of enals in presence of phosphoramidite, SimplePhos, or (R)-BINAP ligands with enantiomeric excesses up to 90% is reported. Moreover, ACA of Grignard reagents afforded moderate to good 1,4-regioselectivities with enantioselectivities up to 90%.