Tetrahedron Letters

A convenient new method to construct 1-alkynyl cyclopropanol and its synthetic application to prepare trisubstituted dienones

Y An, J Liu, HY Jiang, Y Wang, Z Chen

Index: An, Yan; Liu, Jie; Jiang, Hai-Ying; Wang, Yahui; Chen, Zili Tetrahedron Letters, 2008 , vol. 49, # 19 p. 3124 - 3128

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Citation Number: 6

Abstract

A new synthetic route was developed via the nucleophilic addition of lithium alkynylide to 1- arylsulfonyl cyclopropanol 1 to afford 1-alkynyl cyclopropanol, which then reacted with aryl iodide to construct trisubstituted cross-conjugated dienones through a palladium-catalyzed process, where the key steps included the regioselective carbopalladation of arylpalladium (II) intermediate across the triple bond of 1-alkynyl cyclopropanol and the ring opening of ...