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Diastereoselective Chelation-Controlled Additions to β-Silyloxy Aldehydes
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    Diastereoselective Chelation-Controlled Additions to β-Silyloxy Aldehydes
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    P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States
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    Organic Letters

    Cite this: Org. Lett. 2012, 14, 13, 3368–3371
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    https://doi.org/10.1021/ol301354w
    Published June 21, 2012
    Copyright © 2012 American Chemical Society

    Abstract

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    A general diastereoselective method for the addition of dialkylzincs and (E)-di- and (E)-trisubstituted vinylzinc reagents to β-silyloxy aldehydes is presented. This method employs alkyl zinc triflate and nonaflate Lewis acids and affords chelation-controlled products (6:1 to > 20:1 dr).

    Copyright © 2012 American Chemical Society

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    Experimental procedures and full characterization of new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 13 publications.

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    13. Gretchen R. Stanton, Meara C. Kauffman, Patrick J. Walsh. ChemInform Abstract: Diastereoselective Chelation‐Controlled Additions to β‐Silyloxy Aldehydes.. ChemInform 2012, 43 (42) https://doi.org/10.1002/chin.201242054

    Organic Letters

    Cite this: Org. Lett. 2012, 14, 13, 3368–3371
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol301354w
    Published June 21, 2012
    Copyright © 2012 American Chemical Society

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