Aliphatic Claisen rearrangement promoted by organoaluminium reagents

K Takai, I Mori, K Oshima, H Nozaki

Index: Takai; Mori; Oshima; Nozaki Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 2 p. 446 - 451

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Citation Number: 49

Abstract

Organoaluminium compounds, R 3 Al, promote the Claisen rearrangement of allyl vinyl ether derivatives at room temperature under transfer of R or H as a nucleophile to the aldehydic carbon. Treatment of 1-butyl-2-propenyl vinyl ether with a hexane solution of Me 3 Al (1.0 M, 2.2 equiv) in CH 2 ClCH 2 Cl at 25° C afforded 5-decen-2-ol (91% yield, E⁄ Z= 47⁄ 53), which was produced by the [3, 3] sigmatropic rearrangement and successive ...