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From vinyl sulfides, sulfoxides and sulfones to vinyl zirconocene derivatives

2003; Elsevier BV; Volume: 60; Issue: 6 Linguagem: Inglês

10.1016/j.tet.2003.08.074

1464-5416

Shahera Farhat, I. Zouev, Ilan Marek,

Asymmetric Synthesis and Catalysis

An easy and straightforward new method for the preparation of sp2 zirconocene derivatives from a wide range of heterosubstituted alkenes such as vinyl sulfides, sulfoxides and sulfones is described. In all cases, a complete isomerization of the stereochemistry is observed and only the E-isomer is obtained. The reactivity of the resulting vinylic organometallic can be increased by a transmetalation reaction into organocopper, organozinc or organopalladium species and, therefore, several carbon–carbon formation were easily realized.