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A General Catalytic Allylation Using Allyltrimethoxysilane

A General Catalytic Allylation Using Allyltrimethoxysilane

Shingo Yamasaki, Kunihiko Fujii, Reiko Wada, Motomu Kanai, Masakatsu Shibasaki

J Am Chem Soc. 2002 Jun 12;124(23):6536-7.

PMID: 12047165

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 %).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2551839	Allyltrimethoxysilane		2551-83-9	Price

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