π-Allyl Donicity Switch in Catalytic Asymmetric Allylation: Usability of a Robust and Feasible Allyl Methyl Ether

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Author(s)

    • Suzuki Yusuke
    • Graduate School of Pharmaceutical Sciences and Research Center for Materials Science, Nagoya University
    • Iwase Shoutaro
    • Graduate School of Pharmaceutical Sciences and Research Center for Materials Science, Nagoya University
    • Hashimoto Kazuki
    • Graduate School of Pharmaceutical Sciences and Research Center for Materials Science, Nagoya University
    • Tanaka Shinji
    • Graduate School of Pharmaceutical Sciences and Research Center for Materials Science, Nagoya University
    • Kitamura Masato
    • Graduate School of Pharmaceutical Sciences and Research Center for Materials Science, Nagoya University

Abstract

<p>A chiral CpRu(II)/<i>p</i>-TsOH combined catalyst is described for asymmetric allylation that reverses the π-allyl donicity of AllX (All: allyl, X: leaving group) from "AllOAc > AllOPh > AllOH > AllOMe" to "AllOH > AllOMe > AllOPh > AllOAc". This represents a novel deviation from conventional Tsuji–Trost-Pd-based methods that operate under basic conditions. This is the first successful demonstration of endowing reactivity in chemically stable AllOMe, which should significantly expand the scope of synthetic possibilities.</p>

Journal

  • Chemistry Letters

    Chemistry Letters 46(9), 1308-1310, 2017

    The Chemical Society of Japan

Codes

  • NII Article ID (NAID)
    130006067862
  • Text Lang
    ENG
  • ISSN
    0366-7022
  • Data Source
    J-STAGE 
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