The Journal of Organic Chemistry

Selective base-catalyzed rearrangement of epoxides into ketones. Application to. gamma.-keto sulfide synthesis

R Tamura, Y Kusama, D Oda

Index: Tamura, Rui; Kusama, Yukihiro; Oda, Daihei Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 595 - 598

Full Text: HTML

Citation Number: 12

Abstract

A methodology for the selective base-catalyzed isomerization of certain epoxides having a@- proton into ketones is presented.@, y-Epoxy nitro compounds were the substrates for this transformation and underwent a multistep reaction consisting of epoxide ring opening, isomerization of the double bond, elimination of HN02, and addition of PhSH to provide y- keto sulfides in good yields by reacting with PhSNa or a combination of PhSH and EhN. ...