An iterative catalytic route to enantiopure deoxypropionate subunits: asymmetric conjugate addition of grignard reagents to alpha,beta-unsaturated thioesters |
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| Authors: | Des Mazery Renaud Pullez Maddalena López Fernando Harutyunyan Syuzanna R Minnaard Adriaan J Feringa Ben L |
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| Affiliation: | Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands. |
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| 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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