A novel vinyl anion equivalent. An extremely short synthesis of 2-substituted 2-cycloalkenones and prostaglandin key intermediates via destannylselenenylation

S Kusuda, Y Watanabe, Y Ueno…

Index: Kusuda, Shinya; Watanabe, Yoshihiko; Ueno, Yoshio; Toru, Takeshi Journal of Organic Chemistry, 1992 , vol. 57, # 11 p. 3145 - 3152

Full Text: HTML

Citation Number: 19

Abstract

The preparation of a novel vinyl anion equivalent and a new destannylaelenenylation procedure are described. The conjugate. addition of (tributylstanny1) lithiithium to 2- (phenylselen0)-2-~ ycloalkenone~, followed by the trapping of the resulting enolates with allylic halides, and subsequent destannylselenenylation gives 2-substituted 2- cycloalkenonea in high yields, in a onepot procedure. The destannylaelenenylation can ...

 Related Synthetic Route

~%

~%

~%

~%

~%

~%

~%

~%

~%

~%

~%

~%

~%

~%

~%

~45%

~99%

~%

~%

~%

~%