Cu-Catalyzed Highly Stereoselective Syntheses of (E)-δ-Vinyl-homoallylic Alcohols

Stereoselective synthesis of (E)-delta-vinyl-homoallylic alcohols was developed. Starting from alpha-vinyl allylboronate, Cucatalyzed allylation of aldehydes or ketones forms secondary or tertiary delta-vinyl-homoallylic alcohols with high E-selectivities. It is proposed that the reaction operates under the Curtin-Hammett principle via the intermediacy of alpha-vinyl allylic copper species to give the alcohol products with high E-selectivities.

Automated summary

A stereoselective synthesis of (E)-delta-vinyl-homoallylic alcohols has been developed using copper-catalyzed allylation of alpha-vinyl allylboronate with aldehydes or ketones, resulting in high E-selectivities. The reaction proceeds via the Curtin-Hammett principle through the intermediacy of alpha-vinyl allylic copper species to provide the alcohol products with high E-selectivities.