Diels-Alder reaction of α-tropolone and electron-deficient dienophiles prompted by Et3N or silica gel: a new synthetic method of highly functionalized homobarrelenone derivatives

Hiroaki Okamura, Hiroki Iiji, Toshiyuki Hamada, Tetsuo Iwagawa, Hiroshi Furuno

    研究成果: ジャーナルへの寄稿学術誌査読

    15 被引用数 (Scopus)

    抄録

    A Diels-Alder reaction of α-tropolone and electron-deficient dienophiles prompted by Et3N or silica gel was performed. Reaction with the highly reactive dienophile, N-methylmaleimide, proceeded smoothly in the presence of Et3N or silica gel to yield adducts as a mixture of endo and exo isomers. Both catalysts accelerated endo/exo isomerization of the product, and detailed examination of the reaction using hinokitiol and N-methylmaleimide revealed that isomerization proceeds via an intramolecular path without retro Diels-Alder reaction. Successful cycloaddition reactions were established with six other dienophiles: acrylonitrile, methyl acrylate, ethyl vinyl ketone, dimethyl fumalate, dimethyl malate, and dimethyl acetylenedicarboxylate, and the corresponding adducts were obtained in good to moderate yields.

    本文言語英語
    ページ(範囲)10709-10714
    ページ数6
    ジャーナルTetrahedron
    65
    51
    DOI
    出版ステータス出版済み - 12月 19 2009

    !!!All Science Journal Classification (ASJC) codes

    • 生化学
    • 創薬
    • 有機化学

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