Stereoselective Control of the Cu Activation of β,β-Diboryl Acrylates for Allylic Coupling Protocols with Concomitant Lactonization

Identifier:  imarina:9363284

Handle: https://hdl.handle.net/20.500.11797/imarina9363284

Authors:  Pujol, M; Méndez, M; Fernández, E

Abstract:
The key to a successful C-B activation is to discriminate between two geminal boryl moieties that are exposed to the same reaction conditions. Here we describe a stereoselective C-B activation of beta,beta-diboryl acrylates forming exclusively the (Z)-alpha-borylalkenyl copper(I) key intermediate, for subsequent allylic alkylation reactions. The new borylated (Z)-skipped dienoates followed a feasible iodo-lactonization sequence for the preparation of borylated lactone cores, which can be used in drug discovery.