Acid-catalyzed regioselective acylation of. ALPHA.-silylallylic sulfides and its application to a novel cyclopentannelation and furan annelation.

…, H SATO, LIHM CHEN, K KOTSUJI

Index: Hiroi, Kunio; Sato, Hiroyasu; Chen, Lih-Ming; Kotsuji, Kumiko Chemical and Pharmaceutical Bulletin, 1987 , vol. 35, # 4 p. 1413 - 1426

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Citation Number: 4

Abstract

Introduction of a silyl group at the a-position of allylic sulfides, followed by the aluminum chloride-catalyzed reaction of the resulting α-silylallylic sulfides with acid chlorides resulted in regioselective acylation at the γ-position of the allylic system to give γ-acylated vinylic sulfides, chemically equivalent to 1, 4-dicarbonyl compounds. Heating of the products in refluxing benzene with an equimolar amount of p-toluenesulfonic acid produced 2- ...

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