Construction of Bridged and Fused Bicyclic Skeletons via Intramolecular Addition of Nucleophiles to (η4-Diene)Fe(CO)3 Complexes Bearing Functionalized Side Chains

Ming Chang P. Yeh, B. A. Sheu, H. W. Fu, S. I. Tau, L. W. Chuang

Research output: Contribution to journalArticle

76 Citations (Scopus)

Abstract

Reaction of lithium diisopropylamide (LDA) with (η4-1,3-cyclohexadiene)Fe(CO)3 complexes bearing functionalized side chains at C-5, under an atmosphere of carbon monoxide, gives bridged bicyclo[3.2.1]octene and bicyclo[3.3.1]nonene systems after electrophilic quenching, whereas larger rings cannot be obtained in this series. Under the same reaction conditions, intramolecular cyclization of acyclic (η4-1,3-butadiene)Fe(CO)3 complexes with functionalized side chains at the terminal position of the diene ligands furnishes fused bicyclo[3.3.0]octanone and bicyclo[4.3.0]nonanone derivatives after acid quenching. The iron-mediated intramolecular nucleophilic addition allows for the direct stereocontrol of four stereogenic centers of these fused bicyclic skeletons.

Original languageEnglish
Pages (from-to)5941-5952
Number of pages12
JournalJournal of the American Chemical Society
Volume115
Issue number14
DOIs
Publication statusPublished - 1993 Jul 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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