Thermal and palladium-catalyzed [3 + 2] synthesis of cyclopentadienone acetals from cyclopropenone acetals and acetylenes

Hiroyuki Isobe, Sota Sato, Takatsugu Tanaka, Hidetoshi Tokuyama, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

(Chemical Equation Presented) Substituted cyclopentadienone acetals (CPDAs) were synthesized by a thermal or palladium-catalyzed [3 + 2] cycloaddition reaction of a substituted cyclopropenone acetal to an electron-deficient acetylene. The synthesis afforded di-, tri-, and tetrasubstituted CPDAs of considerable structural varieties that undergo Diels-Alder reaction to produce bicyclo[2.2.1]heptenes.

Original languageEnglish
Pages (from-to)3569-3571
Number of pages3
JournalOrganic letters
Volume6
Issue number20
DOIs
Publication statusPublished - 2004 Sep 30
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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