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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1039-1045

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

Hajime Ito, Shinichiro Ito, Yusuke Sasaki, Kou Matsuura and Masaya Sawamura

Department of Chemistry, Faculty of Science, Hokkaido University,Sapporo 060-0810, Japan

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.