Journal of the American Chemical Society, Vol.129, No.42, 12634-12634, 2007
Zirconocene-mediated highly regio- and stereoselective synthesis of multisubstituted olefins starting from 1-alkynylboronates
Multisubstituted olefins are efficiently prepared by the zirconocene-mediated regio- and stereoselective coupling between 1alkynylboronates and ethylene, followed by sequential transformation in moderate to high yields. The proper combination of substrates and reaction conditions is important for high yields. The synthesis of various tetra substituted alkenes in a regio- and stereocontrolled manner is described. This methodology has been applied to the synthesis of (Z )-tamoxifen in a concise, regio and stereoselective manner. This multicomponent coupling strategy involves the characteristics of 1-alkynylboronates toward high selectivities followed by palladium(O)-mediated cross-coupling with aryl halides.