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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1055-1062

Cu(I)-catalyzed asymmetric allylation of ketones and ketimines

Motomu Kanai, Reiko Wada, Tomoyuki Shibuguchi and Masakatsu Shibasaki

Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract: Chiral CuF-catalyzed asymmetric allylation of ketones and ketimines is described. Nucleophile activation via transmetallation (allylboronate to allylcopper), which is facilitated by a cocatalyst [La(OiPr)3 or LiOiPr], is key for these reactions. A CuOTf-3KOtBu-DUPHOS complex is a comparably effective catalyst that reduces the required amount of chiral phosphines.