Base-catalyzed Schmittel cycloisomerization of o-phenylenediyne-linked bis(arenol)s to indeno[1,2-c]chromenes

Masaki Furusawa, Kosuke Arita, Tatsushi Imahori, Kazunobu Igawa, Katsuhiko Tomooka, Ryo Irie

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

We describe the transition metal-free base-catalyzed Schmittel cycloisomerization reactions of o-phenylene-linked bis(arenol)s to indeno[1,2-c]chromene derivatives through prototropic rearrangement (tautomerization) to a putative vinylidene o-quinone methide intermediate with an enyne-allene system followed by a formal inverse-electron-demand hetero Diels-Alder cycloaddition. The preliminary results on catalytic asymmetric cycloisomerization with chiral bases are also disclosed.

Original languageEnglish
Pages (from-to)7107-7110
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number52
DOIs
Publication statusPublished - Dec 25 2013

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Benzopyrans
Cycloaddition
Cycloaddition Reaction
Transition metals
Metals
Electrons
Derivatives
quinone methide
propadiene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Base-catalyzed Schmittel cycloisomerization of o-phenylenediyne-linked bis(arenol)s to indeno[1,2-c]chromenes. / Furusawa, Masaki; Arita, Kosuke; Imahori, Tatsushi; Igawa, Kazunobu; Tomooka, Katsuhiko; Irie, Ryo.

In: Tetrahedron Letters, Vol. 54, No. 52, 25.12.2013, p. 7107-7110.

Research output: Contribution to journalArticle

Furusawa, Masaki ; Arita, Kosuke ; Imahori, Tatsushi ; Igawa, Kazunobu ; Tomooka, Katsuhiko ; Irie, Ryo. / Base-catalyzed Schmittel cycloisomerization of o-phenylenediyne-linked bis(arenol)s to indeno[1,2-c]chromenes. In: Tetrahedron Letters. 2013 ; Vol. 54, No. 52. pp. 7107-7110.
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AU - Tomooka, Katsuhiko

AU - Irie, Ryo

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