Efficient and stereoselective synthesis of β-trifluoromethyl α,β-unsaturated esters via iron(III) porphyrin-catalyzed olefination of ketones

Ying Chen, Lingyu Huang, X. Peter Zhang

Research output: Contribution to journalArticle

Abstract

β-Trifluoromethyl α,β-unsaturated esters were efficiently prepared by reactions of fluorine-containing ketones with diazo compounds via metalloporphyrin-catalyzed olefination in the presence of triphenylphosphine. The commercially available Fe(III)(TPP)Cl (TPP: tetraphenylporphyrin) is effective for catalyzing the olefination of a variety of trifluoromethyl ketones with different diazoacetate esters under mild conditions. The reactions proceeded with high yields (up to 95% isolated yield) and high stereoselectivity (up to 99% (E)-selectivity).

Original languageEnglish (US)
Pages (from-to)5925-5929
Number of pages5
JournalJournal of Organic Chemistry
Volume68
Issue number15
DOIs
StatePublished - Jul 25 2003
Externally publishedYes

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Porphyrins
Ketones
Esters
Iron
Metalloporphyrins
Stereoselectivity
Fluorine
triphenylphosphine
tetraphenylporphyrin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient and stereoselective synthesis of β-trifluoromethyl α,β-unsaturated esters via iron(III) porphyrin-catalyzed olefination of ketones. / Chen, Ying; Huang, Lingyu; Zhang, X. Peter.

In: Journal of Organic Chemistry, Vol. 68, No. 15, 25.07.2003, p. 5925-5929.

Research output: Contribution to journalArticle

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