Catalytic iron-mediated ene carbocyclizations: formal [4+4]-ene reactions of triene esters

James M. Takacs, Peter W. Newsome, Cynthia Kuehn, Fusao Takusagawa

Research output: Contribution to journalArticle

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Abstract

2-Substituted-2,7,9-decatrienoates undergo an iron-catalyzed carbocyclization to yield trans-disubstituted cyclopentanes in moderate-to-good chemical yields. The cyclization products are formally the result of a [4+4]-ene reaction in which cis-propenyl and 2-acroyl functionalities are introduced as appendages to the newly formed cyclopentane ring by the cyclization. Triene ester substrates bearing an alkyl substituent at the 4- or 6-positions cyclize with high 1,2-stereoinduction to yield trisubstituted cyclopentanes in which the relative stereochemistry between three contiguous stereocenters is controlled.

Original languageEnglish (US)
Pages (from-to)5507-5522
Number of pages16
JournalTetrahedron
Volume46
Issue number16
DOIs
StatePublished - 1990

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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