Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions

Ichiro Hayakawa, Yuji Yamanaka, Koichi Mitsudo, Hiromi Ota, Akira Sakakura

Research output: Contribution to journalArticle

Abstract

The reaction of silyl dienol ether of γ-pyrone with dimethyl acetylenedicarboxylate (DMAD) gives the regioselective insertion product in 66% yield. This DMAD-insertion reaction is thought to include a three-step sequence: (1) thermal [2+2]-type cycloaddition reaction of silyl dienol ether of γ-pyrone with DMAD, (2) ring-opening electrocyclic reaction of the cyclobutene skeleton, and (3) hydrolysis of the silyl dienol ether. The present reaction proceeds under mild conditions without any catalysts or heating. In addition, the [2+2]-type cycloaddition reaction proceeds regioselectively at the C3–C4 double bond in the silyl dienol ether of γ-pyrone.

Original languageEnglish
Pages (from-to)2299-2306
Number of pages8
JournalHeterocycles
Volume94
Issue number12
DOIs
Publication statusPublished - Jan 1 2017

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Pyrones
Ether
Heating
Catalysts
Cycloaddition
Cycloaddition Reaction
Skeleton
Hydrolysis
Hot Temperature
acetylenedicarboxylic acid dimethyl ester

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions. / Hayakawa, Ichiro; Yamanaka, Yuji; Mitsudo, Koichi; Ota, Hiromi; Sakakura, Akira.

In: Heterocycles, Vol. 94, No. 12, 01.01.2017, p. 2299-2306.

Research output: Contribution to journalArticle

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