Tetrahedron Letters

Highly regioselective diels-alder reactions of 2-trimethylsilylmethyl-1, 3-butadiene catalyzed by a lewis acid and applications to syntheses of terpenes

A Hosomi, H Iguchi, J Sasaki, H Sakurai

Index: Hosomi, Akira; Iguchi, Hirokazu; Sasaki, Jun-ichi; Sakurai, Hideki Tetrahedron Letters, 1982 , vol. 23, # 5 p. 551 - 554

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Citation Number: 32

Abstract

Abstract 2-Trimethylsilylmethyl-1, 3-butadiene undergoes highly regioselective Diels-Alder reactions with dienophiles such as acrolein and methyl vinyl ketone catalyzed by aluminum chloride in which the “para” isomers are obtained almost exclusively. The adducts are converted readily to a variety of naturally occurring mono and sesquiterpenes.