Highly stereoselective syntheses of (E)-δ-boryl-anti-homoallylic alcohols via allylation with α-boryl-(E)-crotylboronate

Abstract

A highly stereoselective synthesis of (E)-δ-boryl-anti-homoallylic alcohols is developed. In the presence of a Lewis acid, aldehyde allylation with α-boryl-(E)-crotylboronate gave δ-boryl-anti-homoallylic alcohols in good yields with excellent E-selectivity. The E-vinylboronate group in the products provides a useful handle for cross-coupling reactions as illustrated in the fragment synthesis of chaxamycins.