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A General Catalytic Allylation Using Allyltrimethoxysilane
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Section:Abstract
A general and mild catalytic allylation of carbonyl compounds, applicable to aldehydes, ketones, and imines is developed using allyltrimethoxysilane as the allylating reagent. The reaction proceeds smoothly with 1−10 mol % of CuCl and TBAT in THF at ambient temperature. Mechanism studies indicated that the copper alkoxide, allylfluorodimethoxysilane, and allyltrimethoxysilane are essential to promote the reaction efficiently. Preliminary extension of the reaction to the first catalytic enantioselective allylation of ketones using an allylsilane produced the product with 61% ee from acetophenone, using a CuCl-p-tol-BINAP-TBAT catalyst (15 mol %).
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This article has been cited by 44 ACS Journal articles (5 most recent appear below).
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Mild and General Zinc-Alkoxide-Catalyzed Allylations of Ketones with Allyl Pinacol Boronates
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Catalytic Asymmetric Synthesis of R207910
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Yutaka Saga, Rie Motoki, Sae Makino, Yohei Shimizu, Motomu Kanai and Masakatsu ShibasakiJournal of the American Chemical Society2010 132 (23), 7905-7907The first asymmetric synthesis of a very promising antituberculosis drug candidate, R207910, was achieved by developing two novel catalytic transformations; a catalytic enantioselective proton migration and a catalytic diastereoselective allylation of an ...
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History
- Published In Issue June 12, 2002
- Received March 21, 2002
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