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Strikingly Simple Direct α-Allylation of Aldehydes with Allyl Alcohols:  Remarkable Advance in the Tsuji-Trost Reaction

Masanari Kimura, Yoshikazu Horino, Ryutaro Mukai, Shuji Tanaka and Yoshinao Tamaru*

*Department of Applied Chemistry Faculty of Engineering, Nagasaki University Bunkyo-machi, Nagasaki 852-8521, Japan

M. Kimura, Y. Horino, R. Mukai, S. Tanaka, Y. Tamaru, J. Am. Chem. Soc., 2001, 123, 10401-10402.

DOI: 10.1021/ja011656a



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Abstract

Pd catalyzes an α-allylic alkylation of aldehydes with allyl alcohols in the presence of stoichiometric amounts of Et3B, Et3N, and LiCl. This convenient Tsuji-Trost allylation offers mild reaction conditions, wide applicability, and avoids the need for preactivation of both reaction partners.

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proposed mechanism



Key Words

α-Allylation, Tsuji-Trost Reaction


ID: J48-Y2001