Stereoselective Synthesis of (E)-2-En-4-ynoic acids with Ynolates: Catalytic conversion to tetronic acids and 2-pyrones

Takashi Yoshlkawa, Mitsuru Shindo

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

"Chemical Equation Presented" A highly torquoselective olefinatlon of alkynoates to provide functionalized tetrasubstltuted olefins, (E)-2-en-4-ynoic acids, Is described. Addition of Bronsted acids dramatically switched the mode of the Ag(l)-catalyzed cyclization of the resulting enyne carboxylic acids to give either tetronic acids or 2-pyrones.

Original languageEnglish
Pages (from-to)5378-5381
Number of pages4
JournalOrganic Letters
Volume11
Issue number23
DOIs
Publication statusPublished - Dec 3 2009

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acids
Acids
Cyclization
Alkenes
synthesis
Carboxylic Acids
carboxylic acids
alkenes
2-pyrone
tetronic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Stereoselective Synthesis of (E)-2-En-4-ynoic acids with Ynolates : Catalytic conversion to tetronic acids and 2-pyrones. / Yoshlkawa, Takashi; Shindo, Mitsuru.

In: Organic Letters, Vol. 11, No. 23, 03.12.2009, p. 5378-5381.

Research output: Contribution to journalArticle

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