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Protecting-Group-Free Diastereoselective C[BOND]C Coupling of 1,3-Glycols and Allyl Acetate through Site-Selective Primary Alcohol Dehydrogenation

Authors

  • Dr. Anne-Marie R. Dechert-Schmitt,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA)
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  • Dr. Daniel C. Schmitt,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA)
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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)
    • University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA)

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  • Acknowledgements is made to the Robert A. Welch Foundation (F-0038) and the NIH-NIGMS (RO1-GM093905) for financial support. The Cancer Prevention Research Institute of Texas (CPRIT) is acknowledged for Postdoctoral Fellowship support (D.C.S.). Dr. Taichiro Touge of Takasago is thanked for the generous donation of segphos ligands.

Abstract

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Eine ausgeprägte kinetische Präferenz für die Dehydrierung einer primären Alkoholgruppe ermöglicht ortsselektive iridiumkatalysierte C-C-Kupplungen von Polyolen mit Allylacetat ohne Schutzgruppen, metallierte Reagentien, chirale Auxiliare oder gezielte Oxidation zum Aldehyd.

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