Stereoselective Intramolecular Dearomatizative [4+2] Cycloaddition of Linked Ethynylnaphthol–Benzofuran Systems

Shota Beppu, Sachie Arae, Masaki Furusawa, Kosuke Arita, Hitoshi Fujimoto, Michinori Sumimoto, Tatsushi Imahori, Kazunobu Igawa, Katsuhiko Tomooka, Ryo Irie

研究成果: Contribution to journalArticle査読

13 被引用数 (Scopus)

抄録

A base-catalyzed stereoselective intramolecular dearomatizative [4+2] cycloaddition of o-phenylene-linked ethynylnaphthol–benzofuran systems was explored. In this reaction, we presume the involvement of electrophilic vinylidene o-quinone methides (4π), which add across the electron-rich furan double bonds (2π) to produce elaborate, fused oxa-polyheterocyclic frameworks with consecutive quaternary and tertiary asymmetric carbon atoms as single diastereomers. The catalytic and enantioselective synthesis of these chiral fused polyheterocyclic structures is also feasible with the use of a prevalent cinchonidine or cinchonine chiral base.

本文言語英語
ページ(範囲)6914-6918
ページ数5
ジャーナルEuropean Journal of Organic Chemistry
2017
46
DOI
出版ステータス出版済み - 12 15 2017

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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