Intramolecular formal iron-catalyzed ene reactions: The stereoselective and regiocontrolled formation of substituted tetrahydropyrans

James M. Takacs, Lawrence G. Anderson, Mark W. Creswell, Beckie E. Takacs

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

The iron-catalyzed six-membered ring carbocyclizations of 5-oxa-2, 8, 10-undecatriene derivatives proceed with high regio- and stereoselectivity to yieldtrans-3, 4-disubstituted tetrahydropyrans. Substrates containing an alkyl substituent at the 4- or the 7-position of the starting triene ether cyclize with high secondary stereoinduction to producetrans, trans-trisubstituted derivatives. Diastereomeric (2Z)- and (2E)-substrates cyclize via complementary [4+4]- and [4+2]-ene reaction pathways.

Original languageEnglish (US)
Pages (from-to)5627-5630
Number of pages4
JournalTetrahedron Letters
Volume28
Issue number46
DOIs
StatePublished - 1987

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Ether
Iron
Derivatives
Stereoselectivity
Regioselectivity
Substrates

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Intramolecular formal iron-catalyzed ene reactions : The stereoselective and regiocontrolled formation of substituted tetrahydropyrans. / Takacs, James M.; Anderson, Lawrence G.; Creswell, Mark W.; Takacs, Beckie E.

In: Tetrahedron Letters, Vol. 28, No. 46, 1987, p. 5627-5630.

Research output: Contribution to journalArticle

Takacs, James M. ; Anderson, Lawrence G. ; Creswell, Mark W. ; Takacs, Beckie E. / Intramolecular formal iron-catalyzed ene reactions : The stereoselective and regiocontrolled formation of substituted tetrahydropyrans. In: Tetrahedron Letters. 1987 ; Vol. 28, No. 46. pp. 5627-5630.
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