Tetrahedron letters

Facile generation method for conjugated allenyl esters based on retro-Dieckmann-type ring-opening reactions

S Sano, H Shimizu, Y Nagao

Index: Sano, Shigeki; Shimizu, Hisashi; Nagao, Yoshimitsu Tetrahedron Letters, 2005 , vol. 46, # 16 p. 2883 - 2886

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Citation Number: 13

Abstract

α-Alkynyl-α-ethoxycarbonyl cyclopentanones 1a–c and cyclohexanones 2a–c were readily synthesized by the reaction of ethyl 2-oxocyclopentanonecarboxylate 6 and ethyl 2- oxocyclohexanonecarboxylate 7 with alkynyllead triacetates 5a–c obtained from lithium acetylides 4a–c and lead tetraacetate. Treatment of 1a–c and 2a–c with 1N KOH in THF or with n-Bu4N+ OEt− in EtOH and THF gave the corresponding conjugated allenyl esters 8a ...