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A General Catalytic Allylation Using Allyltrimethoxysilane

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

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan, Email: mshibasamol.f.u-tokyo.ac.jp

S. Yamasaki, K. Fujii, R. Wada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2002, 124, 6536-6537.

DOI: 10.1021/ja0262582 (free Supporting Information)


Abstract

A general and mild CuCl-TBAT-catalyzed allylation of aldehydes, ketones, and imines was developed using allyltrimethoxysilane as the allylating reagent. Mechanism studies indicated that the copper alkoxide, allylfluorodimethoxysilane, and allyltrimethoxysilane are essential to promote the reaction efficiently.

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Key Words

Hosomi-Sakurai Reaction, Homoallylic Amines, Homoallylic Alcohols


Catalytic Enantioselective Allylboration of Ketones

R. Wada, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2004, 126, 8910-8911.

DOI: 10.1021/ja0262582 (free Supporting Information)


ID: J48-Y2002-1130