Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates

Abstract

A copper-catalyzed conjugate addition of alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) to alkynoates to form β-disubstituted acrylates is reported. The addition occurred in a formal syn-hydroalkylation mode. The syn stereoselectivity was excellent regardless of the substrate structure. A variety of functional groups were compatible with the conjugate addition.

Keywords

• alkylborane
• alkynoate
• conjugate addition
• copper
• multisubstituted alkene