Tetrahedron letters

Strictly regio-controlled method for α-alkenylation of cyclic ketones via palladium-catalyzed cross coupling

E Negishi, ZR Owczarczyk, DR Swanson

Index: Negishi, Ei-ichi; Owczarczyk, Zbyslaw R.; Swanson, Douglas R. Tetrahedron Letters, 1991 , vol. 32, # 35 p. 4453 - 4456

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Citation Number: 81

Abstract

Abstract Cyclic α-iodoenones and α-triflyloxyenones, but not α-bromoenones, smoothly react with alkenylzinc and related derivatives in the presence of a catalytic amount of a palladium- phosphine complex, such as Pd (PPh 3) 4 or Cl 2 Pd (PPh 3) 2 treated with n-BuLi (2 equiv), to give α-alkenylenones which can be conjugately reduced to the corresponding α-alkenyl ketones with complete retention of both enone regiochemistry and alkenyl stereochemistry.