Stereoretentive Suzuki–Miyaura and Kumada–Tamao–Corriu Cross-Couplings for Preparing (E)- and (Z)-Stereodefined, Fully Substituted α,β-Unsaturated Esters: Application for a Pharmacophore Synthesis

DOI PDF 被引用文献3件
  • Yoo Tanabe
    Department of Chemistry, School of Science and Technology, Kwansei Gakuin University
  • Yuka Sato
    Department of Chemistry, School of Science and Technology, Kwansei Gakuin University
  • Yuichiro Ashida
    Department of Chemistry, School of Science and Technology, Kwansei Gakuin University
  • Daisuke Yoshitake
    Department of Chemistry, School of Science and Technology, Kwansei Gakuin University
  • Mayuko Hoshino
    Department of Chemistry, School of Science and Technology, Kwansei Gakuin University
  • Taichi Takemoto
    Department of Chemistry, School of Science and Technology, Kwansei Gakuin University

説明

<jats:p>Substrate-general stereocomplementary Suzuki–Miyaura (SM) cross-coupling and relevant Kumada–Tamao–Corriu (KTC) cross-coupling reactions for preparing (E)- and (Z)-stereodefined, fully substituted α,β-unsaturated esters are described. The SM cross-coupling reactions were performed under Pd(OAc)2/SPhos/iPr2NEt catalysis (24 examples, 66–99% yield). The KTC cross-coupling reactions were also performed under similar Pd(OAc)2/SPhos conditions (11 examples, 50–98% yield). Application to a useful pharmacophore containing a cyclopropane structure was investigated, wherein distinctive (E)- and (Z)-stereochemical difference between XPhos and SPhos was observed. A plausible mechanism for the stereoretention and stereoinversion cross-coupling reactions is proposed.</jats:p>

収録刊行物

  • Synthesis

    Synthesis 50 (23), 4659-4667, 2018-08-23

    Georg Thieme Verlag KG

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