Diastereoselective allylation of aldehydes with an enantiopure 2-sulfinylallyl halide under environmentally friendly Barbier-type conditions
[reaction: see text] A simple, efficient, and diastereoselective zinc-promoted allylation of aldehydes with enantiopure (Ss)-3-chloro-2-(p-tolylsulfinyl)-1-propene [(Ss)-1] under aqueous Barbier conditions is described. The observed diastereoselectivity can be explained via an acyclic antiperiplanar transition state model.
Marquez
F
Facultat de Farmacia, Unitat de Quimica Farmaceutica, Universitat de Barcelona, Spain.
Llebaria
A
Delgado
A