Diastereoselective Synthesis of Nitrogen-Containing Heterobicyclic and -tricyclic Skeletons via Intramolecular Cyclization of (η4-diene)Fe(CO)3 Complexes Bearing Amino Acid Derivatives

Ming Chang P. Yeh, L. W. Chuang, C. C. Hwu, J. M. Sheu, L. C. Row

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20 Citations (Scopus)


Addition of secondary amino acid derivatives to (η5-pentadienyl)tricarbonyliron cations gives (η4-diene)tricarbonyliron complexes in high yields with amino ester groups at the terminal position of the diene ligands. Treatments of the adducts containing a sarcosine, phenylalanine, or alanine moiety with lithium diisopropylamide (LDA), under an atmosphere of carbon monoxide, furnish fused 3-azabicyclo[3.3.0]octanecarboxylic acid derivatives. Under the same reaction conditions, intramolecular cyclizations of complexes containing a proline or pipecolinic acid derivative at the terminal position of the diene ligands give 6-azatricyclo['6]undecane and 7-azatricyclo['7]dodecane ring systems, respectively, whereas treatment of the complex containing a nipecotic acid derivative provides a bridged 8-azatricyclo['6]dodecanecarboxylic acid derivative.

Original languageEnglish
Pages (from-to)3396-3407
Number of pages12
Issue number7
Publication statusPublished - 1995 Jul


ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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