Catalytic Enantioselective Allylboration of Ketones

Reiko Wada,† Kounosuke Oisaki,† Motomu Kanai,*†‡ and Masakatsu Shibasaki*†
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan, and PRESTO, Japan Science and Technology Corporation, Japan
J. Am. Chem. Soc., 2004, 126 (29), pp 8910–8911
DOI: 10.1021/ja047200l
Publication Date (Web): July 1, 2004
Copyright © 2004 American Chemical Society
†

 The University of Tokyo.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 PRESTO.

, mshibasa@mol.f.u-tokyo.ac.jp

Abstract

Abstract Image

The first example of catalytic enantioselective allylboration and crotylboration of simple ketones is described. High enantioselectivity (up to 93% ee) was obtained using 3 mol % CuF−iPr-DuPHOS as a chiral catalyst and 4.5 mol % La(OiPr)3 as a cocatalyst. Mechanistic studies strongly suggested that the active nucleophile of the present reaction is an allylcopper, and that La(OiPr)3 facilitates the generation of an active allylcopper from the allylboronate, without affecting the transition-state structure of the ketone allylation step.

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History

  • Published In Issue July 28, 2004
  • Received May 13, 2004

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