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Regioselective Base-Free Intermolecular Aminohydroxylations of Hindered and Functionalized Alkenes

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    Regioselective Base-Free Intermolecular Aminohydroxylations of Hindered and Functionalized Alkenes
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    Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States
    *E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2012, 77, 2, 1208–1214
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    https://doi.org/10.1021/jo202375a
    Published December 21, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    Regioselective base-free intermolecular aminohydroxylations of functionalized trisubstituted and 1,1-disubstituted alkenes employing benzoyloxycarbamate 3a and catalytic OsO4 are described. In all cases, the more substituted alcohol isomer is favored. Sluggish reactions could be promoted by gentle heating, the use of amine ligands, or increased catalyst loadings. A competitive rearrangement was observed with a secondary allylic alcohol substrate. The adducts serve as useful precursors to dehydroamino acids.

    Copyright © 2011 American Chemical Society

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    Supporting Information

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    Structure proofs of 33a and 33b, stereochemical assignments of 35a–c, and copies of 1H and 13C NMR spectra for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2012, 77, 2, 1208–1214
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo202375a
    Published December 21, 2011
    Copyright © 2011 American Chemical Society
    Request reuse permissions

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