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

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

Renaud Des Mazery  1 , Maddalena Pullez, Fernando López, Syuzanna R Harutyunyan, Adriaan J Minnaard, Ben L Feringa
Affiliations

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

Renaud Des Mazery et al. J Am Chem Soc. .

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.

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