An expedient stereoselective synthesis of (E)-α,β-unsaturated esters and thioesters using FeCl3·6H2O

Amar R. Mohite, Trimbak B. Mete, Ramakrishna G. Bhat

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Facile and convenient synthesis of α,β-unsaturated esters and thioesters from alkylidene derivatives of Meldrum's Acid is described. This method uses catalytic amount of FeCl3·6H2O (0.001–0.005 equiv) with alcohols/thiols (1 equiv) in dry CH3NO2 followed by catalytic amount of piperidine. A variety of α,β-unsaturated esters and thioesters have been synthesized with high E-stereoselectivity in good to excellent yields. The application of this methodology is demonstrated by gram scale synthesis of octinoxate, a sunscreen agent, and other p-methoxycinnamate esters.

Original languageEnglish
Pages (from-to)770-774
Number of pages5
JournalTetrahedron Letters
Volume58
Issue number8
DOIs
StatePublished - 1 Jan 2017
Externally publishedYes

Keywords

  • Iron chloride
  • Meldrum's acid
  • Microwave
  • Sun screen filter
  • α,β-unsaturated esters

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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