Copper(I)-Catalyzed Dehydrative C-Glycosidation of Unprotected Pyranoses with Ketones

DOI Web Site 被引用文献4件 参考文献38件
  • XiaoFeng Wei
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
  • ShiLiang Shi
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
  • XiaoWei Xie
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
  • Yohei Shimizu
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
  • Motomu Kanai
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

書誌事項

公開日
2016-09-09
資源種別
journal article
DOI
  • 10.1021/acscatal.6b02106
公開者
American Chemical Society (ACS)

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説明

We developed a copper(I)-catalyzed diastereoselective incorporation of ketones into unprotected pyranoses. The reactivity was dependent on the bite angle of the diphosphine ligand in the copper catalyst, and we identified an achiral diphosphine ligand L1 bearing an exceptionally large bite angle as the optimal ligand. A copper(I)-conjugated Brϕnsted base catalyst containing ligand L1 enabled the C–C bond-forming reaction via in situ-generated copper(I) enolate, even in the presence of multiple unprotected hydroxy groups. A variety of ketones were introduced with high diastereoselectivity. The product 2,6-cis-pyrans has many applications for the synthesis of biologically active molecules.

収録刊行物

  • ACS Catalysis

    ACS Catalysis 6 (10), 6718-6722, 2016-09-09

    American Chemical Society (ACS)

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