Synfacts 2007(8): 0825-0825  
DOI: 10.1055/s-2007-968731
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Allylic Alkylations for the Synthesis of Chiral Allylsilanes

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

Publication History

Publication Date:
24 July 2007 (online)

Significance

Allylsilanes are useful intermediates in stereoselective synthesis. The paper presents a method for the generation of chiral tertiary or quaternary allylsilanes. It involves a copper-catalyzed allylic alkylation with organozinc reagents in the presence of silver-carbene complexes. The substrate reacts in nearly all cases with exclusive SN2′ reactivity to yield chiral allylsilanes in good yields and enantioselectivities.