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Activation of Vinyl Iodides for the Highly Enantioselective Addition to Aldehydes

Authors

  • Dr. Albert M. DeBerardinis,

    1. Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319 (USA), Fax: (+1) 434-924-3710
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  • Mark Turlington,

    1. Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319 (USA), Fax: (+1) 434-924-3710
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  • Prof. Lin Pu

    Corresponding author
    1. Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319 (USA), Fax: (+1) 434-924-3710
    • Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319 (USA), Fax: (+1) 434-924-3710
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  • The partial support of the US National Science Foundation (CHE-0717995 and ECCS-0708923) for this work is gratefully acknowledged.

Abstract

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Mild and tolerant: Vinylzinc reagents were directly prepared from the reaction of vinyl iodides with ZnEt2 under mild reaction conditions. The compound (S)-1 was found to catalyze the addition of the vinylzinc reagents to a variety of aldehydes to generate structurally diverse allylic alcohols with high yields and enantioselectivities. This catalytic process can tolerate functional groups such as esters, chlorine, ethers, and silyl ethers on the substrates. acac=acetylacetonate, NMP=N-methyl-2-pyrrolidone.

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