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
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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. ...
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