Copper-catalyzed substitution of allylic carbonates with diboron: A new approach to allylboronate synthesis

Abstract

Copper-catalyzed γ-selective substitution of allylic carbonates with diboron provides a new method for the efficient synthesis of allylboronates. Optically active α-chiral allylboronates were synthesized through the reaction of chiral allylic carbonates with bis(pinacolato)diboron in the presence of achiral Cu(I)-catalyst with highly efficient chirality transfer. Additionally, in the presence of a chiral Cu(I) catalyst, optically active α-chiral allylboronates were obtained with >90% ee through the reaction of prochiral substrates with the diboron. © 2008 IUPAC.