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

A highly stereoselective synthesis of (E)-delta-boryl-anti-homoallylic alcohols is developed. In the presence of a Lewis acid, aldehyde allylation with alpha-boryl-(E)-crotylboronate gave delta-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.

Automated summary

A highly stereoselective synthesis of (E)-delta-boryl-anti-homoallylic alcohols has been developed 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.