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

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6914-6918
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number46
DOIs
Publication statusPublished - Dec 15 2017

Fingerprint

Cycloaddition
furans
cycloaddition
quinones
vinylidene
Carbon
Atoms
Electrons
carbon
synthesis
atoms
electrons
cinchonine
cinchonidine
quinone methide
furan

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Stereoselective Intramolecular Dearomatizative [4+2] Cycloaddition of Linked Ethynylnaphthol–Benzofuran Systems. / Beppu, Shota; Arae, Sachie; Furusawa, Masaki; Arita, Kosuke; Fujimoto, Hitoshi; Sumimoto, Michinori; Imahori, Tatsushi; Igawa, Kazunobu; Tomooka, Katsuhiko; Irie, Ryo.

In: European Journal of Organic Chemistry, Vol. 2017, No. 46, 15.12.2017, p. 6914-6918.

Research output: Contribution to journalArticle

Beppu, Shota ; Arae, Sachie ; Furusawa, Masaki ; Arita, Kosuke ; Fujimoto, Hitoshi ; Sumimoto, Michinori ; Imahori, Tatsushi ; Igawa, Kazunobu ; Tomooka, Katsuhiko ; Irie, Ryo. / Stereoselective Intramolecular Dearomatizative [4+2] Cycloaddition of Linked Ethynylnaphthol–Benzofuran Systems. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 46. pp. 6914-6918.
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