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Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level

Authors

  • Xin Gao,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
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  • Dr. Yong Jian Zhang,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
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  • Prof. Michael J. Krische

    Corresponding author
    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
    • University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
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  • Acknowledgements is made to the Robert A. Welch Foundation (F-0038) and the NIH-NIGMS (RO1-GM069445). Y.J.Z. acknowledges partial financial support from Shanghai Jiao Tong University.

Abstract

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A flourish of fluorine: Exposure of α-trifluoromethyl allyl benzoate to alcohols in the presence of an ortho-cyclometalated iridium catalyst results in the generation of aldehyde–allyliridium intermediates to form enantiomerically enriched products of anti-(α-trifluoromethyl)allylation. An identical set of products is obtained from aldehydes under related transfer hydrogenation conditions employing isopropyl alcohol as terminal reductant.

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