An iterative catalytic route to enantiopure deoxypropionate subunits: asymmetric conjugate addition of grignard reagents to alpha,beta-unsaturated thioesters

Renaud Des Mazery; Maddalena Pullez; Fernando López; Syuzanna R Harutyunyan; Adriaan J Minnaard; Ben L Feringa

doi:10.1021/ja053020f

An iterative catalytic route to enantiopure deoxypropionate subunits: asymmetric conjugate addition of grignard reagents to alpha,beta-unsaturated thioesters

J Am Chem Soc. 2005 Jul 20;127(28):9966-7. doi: 10.1021/ja053020f.

Authors

Renaud Des Mazery¹, Maddalena Pullez, Fernando López, Syuzanna R Harutyunyan, Adriaan J Minnaard, Ben L Feringa

Affiliation

¹ Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

PMID: 16011337
DOI: 10.1021/ja053020f

Abstract

A highly enantioselective (up to 96% ee) conjugate addition of Grignard reagents, in particular, MeMgBr, to alpha,beta-unsaturated thioesters is provided as well as its application to a diastereo- and enantioselective iterative route to syn- and anti-1,3-dimethyl arrays and deoxypropionate subunits. The versatility of the method is illustrated in the synthesis of (-)-lardolure, a multimethyl-branched insect natural pheromone.