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Stereoselective Syntheses of Trisubstituted Olefins via Platinum Catalysis: α-Silylenones with Geometrical Complementarity

Douglas A. Rooke and Eric M. Ferreira*

*Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, Email: emferrmail.colostate.edu

D. A. Rooke, E. M. Ferreira, J. Am. Chem. Soc., 2010, 132, 11926-11928.

DOI: 10.1021/ja1058197 (free Supporting Information)


Abstract

The use of a catalytic amount of PtCl2 enables the conversion of α-hydroxypropargylsilanes to (Z)-silylenones through a highly selective silicon migration via alkyne activation. The complementary (E)-silylenones are accessed by a regioselective hydrosilylation of the ynone precursor.


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Key Words

Vinylsilanes, Triethylsilane


ID: J48-Y2010-2430