Chemistry Letters

A novel method for cyclopentannelation using regioselective acylation of allylic sulfides via. ALPHA.-silyl intermediates.

K Hiroi, H Sato, K Kotsuji

Index: Hiroi, Kunio; Sato, Hiroyasu; Kotsuji, Kumiko Chemistry Letters, 1986 , p. 743 - 746

Full Text: HTML

Citation Number: 8

Abstract

An aluminum chloride-catalyzed reaction of 1-(phenylthiotrimethylsilylmethyl) cyclohexene, readily obtainable from cyclohexanone, with acid chlorides in dichloromethane underwent a regioselective acylation at the γ-Position of the allylic system to give γ-acyl enol thioethers in good yields. Heating of these enol thioethers with an equimolar amount of p-toluenesulfonic acid produced 2-cyclopentenone derivatives. This novel method for cyclopentannelation ...

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

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

[2, 3]-Sigmatropic rearrangement of an in situ prepared ylide and a thio ether to thio ester conversion as key steps in short syntheses of sarkomycin and its phenyl thio …

[Cohen, Theodore; Kosarych, Zenyk; Suzuki, Kunio; Yu, Lin-Chen Journal of Organic Chemistry, 1985 , vol. 50, # 16 p. 2965 - 2968]

A highly efficient synthetic route to ketones through sequential coupling reactions of grignard reagents with s-phenyl carbonochloridothioate in the presence of nickel …

[Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L. Tetrahedron Letters, 1985 , vol. 26, # 30 p. 3595 - 3598]