Diastereoselective allylation of aldehydes with an enantiopure 2-sulfinylallyl halide under environmentally friendly Barbier-type conditions

F Marquez; A Llebaria; A Delgado

doi:10.1021/ol991412j

Diastereoselective allylation of aldehydes with an enantiopure 2-sulfinylallyl halide under environmentally friendly Barbier-type conditions

Org Lett. 2000 Feb 24;2(4):547-9. doi: 10.1021/ol991412j.

Authors

F Marquez¹, A Llebaria, A Delgado

Affiliation

¹ Facultat de Farmacia, Unitat de Quimica Farmaceutica, Universitat de Barcelona, Spain.

PMID: 10814373
DOI: 10.1021/ol991412j

Abstract

[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.