Synthesis of Functionalized Medium‐Sized <i>trans</i>‐Cycloalkenes by 4π Electrocyclic Ring Opening/Alkylation Sequence

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  • Tomohiro Ito
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida Sakyo-ku Kyoto 606-8501 Japan
  • Masaki Tsutsumi
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida Sakyo-ku Kyoto 606-8501 Japan
  • Ken‐ichi Yamada
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida Sakyo-ku Kyoto 606-8501 Japan
  • Hiroshi Takikawa
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida Sakyo-ku Kyoto 606-8501 Japan
  • Yousuke Yamaoka
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida Sakyo-ku Kyoto 606-8501 Japan
  • Kiyosei Takasu
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida Sakyo-ku Kyoto 606-8501 Japan

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<jats:title>Abstract</jats:title><jats:p>Development of a novel synthetic method for medium‐sized <jats:italic>trans</jats:italic>‐cycloalkenes (TCAs) is described. Functionalized TCAs are readily prepared from simple cycloalkanones in a few steps, namely, enol silyl ether formation, [2+2] cycloaddition, and domino 4π electrocyclic ring opening/alkylation (conjugate addition). The first example of central‐to‐planar chirality transfer from enantiomerically enriched cyclobutenes to TCAs is also described.</jats:p>

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