A general catalytic allylation using allyltrimethoxysilane.
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 %).
Yamasaki
Shingo
S
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
Fujii
Kunihiko
K
Wada
Reiko
R
Kanai
Motomu
M
Shibasaki
Masakatsu
M