Stereoselective carbonyl-olefination via organosilicon compounds

Y Yamakado, M Ishiguro, N Ikeda…

Index: Yamakado, Yoshihiko; Ishiguro, Masaharu; Ikeda, Nobuo; Yamamoto, Hisashi Journal of the American Chemical Society, 1981 , vol. 103, # 18 p. 5568 - 5570

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Citation Number: 103

Abstract

Since the syn elimination of the fl-oxido trialkylsilyl derivative is well established,'an explanation for the observed stereoselectivity must be attributed to the diastereoselective addition of the a-silyl carbanion to the carbonyl compound (Scheme I). Given the reasonable postulate that the reaction proceeds via a pericyclic the influence of variable steric parameters may be analyzed to determine their effects upon the relative heats of formation ...

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