Stereospecific Synthesis of α-Hydroxy-Cyclopropylboronates from Allylic Epoxides

Abstract

Herein, we report a catalytic and stereospecific method for the preparation of enantioenriched α-hydroxy cyclopropylboronates with control in four contiguous stereocenters. The reaction involves the borylation of readily available allylic epoxides using an inexpensive Cu(I) salt and a commercially available phosphine ligand. High diastereocontrol is achieved and different diastereomers can be selectively prepared. Functionalization of the carbon-boron bond provides access to different enantiomerically enriched trisubstituted cyclopropanes from a common intermediate.

Keywords: allylic epoxide; boron; copper; cyclopropane; cyclopropylboronate.