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

34 Scopus citations

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Intramolecular formal iron-catalyzed ene reactions: The stereoselective and regiocontrolled formation of substituted tetrahydropyrans'. Together they form a unique fingerprint.

  • Cite this