Catalytic Enantioselective Allylboration of Ketones
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- 1 July 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (29) , 8910-8911
- https://doi.org/10.1021/ja047200l
Abstract
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.Keywords
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