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

Takashi Yoshlkawa; Mltsuru Shindo

doi:10.1021/ol902086t

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

Takashi Yoshlkawa, Mltsuru Shindo

Department of Fundamental Organic Chemistry

Research output: Contribution to journal › Article › peer-review

39 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 language	English
Pages (from-to)	5378-5381
Number of pages	4
Journal	Organic letters
Volume	11
Issue number	23
DOIs	https://doi.org/10.1021/ol902086t
Publication status	Published - Dec 3 2009

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol902086t

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

Abstract

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