Copper-Catalyzed Allylic Alkylations for the Synthesis of Chiral Allylsilanes

M. A. Kacprzynski; T. L. May; S. K. Kazane; A. H. Hoveyda

doi:10.1055/s-2007-968731

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Synfacts 2007(8): 0825-0825
DOI: 10.1055/s-2007-968731

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

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

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Publication History

Publication Date:
24 July 2007 (online)

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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 S_N2′ reactivity to yield chiral allylsilanes in good yields and enantioselectivities.