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