Ruthenium-catalyzed cycloisomerization of cis-3-En-1-ynes to cyclopentadiene and related derivatives through a 1, 5-sigmatropic hydrogen shift of ruthenium- …

S Datta, A Odedra, RS Liu

Index: Lian, Jian-Jou; Odedra, Arjan; Wu, Chang-Jung; Liu, Rai-Shung Journal of the American Chemical Society, 2005 , vol. 127, # 12 p. 4186 - 4187

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Citation Number: 43

Abstract

We report a new ruthenium-catalyzed cycloisomerization of unactivated cis-3-en-1-ynes, which produces substituted cyclopentadiene and related derivatives. The mechanism of this cyclization is proposed to involve a [1, 5]-sigmatropic hydrogen shift of ruthenium-vinylidene intermediates on the basis of deuterium-labeling experiments.