Tetrahedron letters

Acetal-induced cleavage of carbon-carbon bond of MEM ethers of (E)-4-alkyl-1-trimethylsilyl-1-alken-4-ols providing ketones

Y Horiuchi, M Taniguchi, K Oshima, K Utimoto

Index: Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro Tetrahedron Letters, 1994 , vol. 35, # 43 p. 7977 - 7980

Full Text: HTML

Citation Number: 8

Abstract

Abstract Treatment of methoxyethoxymethyl (MEM) ether of (E)-4-hexyl-1-trimethylsilyl-1- decen-4-ol with titanium (IV) chloride at− 78 C afforded 7-tridecanone in 92% yield under cleavage of carbon-carbon bond. The new method was applied to the conversion of epoxides into ketones.