Tetrahedron

Chemistry of organosilicon compounds—165: 2-Trimethylsilyl-methyl-1, 3-Butadiene—A versatile building block for terpene synthesis

A Hosomi, M Saito, K Sasaki, H Iguchi, JI Sasaki…

Index: Sakurai, Hideki; Hosomi, Akira; Saito, Masaki; Sasaki, Koshi; Iguchi, Hirokazu; et al. Tetrahedron, 1983 , vol. 39, # 6 p. 883 - 894

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Citation Number: 72

Abstract

Two types of synthetically useful reactions of 2-trimethylsilylmethyl-1, 3-butadiene (7) are discussed. Reactions of 7 with acid chlorides, aldehydes, ketones and acetals activated by a Lewis acid give isoprenylated compounds, while 7 undergoes the Diels-Alder reaction with dienophiles. High regiospecificity of the reaction qualifies 7 for a versatile building block of terpene synthesis.