Synfacts 2007(10): 1060-1060  
DOI: 10.1055/s-2007-983894
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral β-Silylketones andE-Allylsilanes

Contributor(s): Mark Lautens, Frédéric Ménard
M. A. Kacprzynski, S. A. Kazane, T. L. May, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
Further Information

Publication History

Publication Date:
07 November 2007 (online)

Significance

A method that accomplishes the asymmetric conjugate addition of both alkyl and aryl zinc nucleophiles on acyclic systems is reported. The authors stress that commercial-grade reagents and catalysts can be used without special precautions. The enantioenriched β-silylketones 2 were shown to be useful synthetic precursors. Of particular interest is the stereoselective preparation of E-allylsilanes 5 and 6 via organometallic cross-couplings of enol triflate 4.