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

39 Citations (Scopus)

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 - Jan 1 1990

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Cyclopentanes
Esters
Iron
Cyclization
Bearings (structural)
Stereochemistry
Substrates

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Catalytic iron-mediated ene carbocyclizations : formal [4+4]-ene reactions of triene esters. / Takacs, James M; Newsome, Peter W.; Kuehn, Cynthia; Takusagawa, Fusao.

In: Tetrahedron, Vol. 46, No. 16, 01.01.1990, p. 5507-5522.

Research output: Contribution to journalArticle

Takacs, James M ; Newsome, Peter W. ; Kuehn, Cynthia ; Takusagawa, Fusao. / Catalytic iron-mediated ene carbocyclizations : formal [4+4]-ene reactions of triene esters. In: Tetrahedron. 1990 ; Vol. 46, No. 16. pp. 5507-5522.
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