Lewis Acid-Mediated Decarboxylative Allylation of Enol Carbonates

Yoichi Dokai, Takuma Nishizawa, Kodai Saito, Tohru Yamada

研究成果: Article査読

抄録

A homoallylic ketone can be transformed and functionalized by various synthetic reactions, and thus, is regarded as one of the representative building blocks in organic chemistry. An additional route to access homoallylic ketones, namely, a Lewis acid-mediated decarboxylative allylation of cyclic enol carbonates, prepared by fixation of carbon dioxide onto propargyl alcohols, was developed in this work. The treatment of a cyclic enol carbonate with a Lewis acid in the presence of an allylsilane resulted in the formation of a homoallylic ketone. It was found that the title reaction proceeded well by the combined use of zirconium tetrachloride with allyltrimethylsilane. The allylation occurred with high regioselectivity and the corresponding homoallylic ketones were obtained in good-to-high yields. A reaction mechanism involving the decarboxylative formation of an oxyallyl cation equivalent is proposed.

本文言語English
論文番号e2100065
ジャーナルHelvetica Chimica Acta
104
7
DOI
出版ステータスPublished - 2021 7

ASJC Scopus subject areas

  • 触媒
  • 生化学
  • 創薬
  • 物理化学および理論化学
  • 有機化学
  • 無機化学

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