An Iterative Catalytic Route to Enantiopure Deoxypropionate Subunits: Asymmetric Conjugate Addition of Grignard Reagents to α,β-Unsaturated Thioesters
Journal of the American Chemical Society2005Vol. 127(28), pp. 9966–9967
Citations Over TimeTop 10% of 2005 papers
Renaud Des Mazery, Maddalena Pullez, Fernando López, Syuzanna R. Harutyunyan, Adriaan J. Minnaard, Ben L. Feringa
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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