Diastereoselective Synthesis of Nitrogen-Containing Heterobicyclic and -tricyclic Skeletons via Intramolecular Cyclization of (η 4 -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

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Addition of secondary amino acid derivatives to (η 5 -pentadienyl)tricarbonyliron cations gives (η 4 -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[6.3.0.0 2 ' 6 ]undecane and 7-azatricyclo[7.3.0.0 2 ' 7 ]dodecane ring systems, respectively, whereas treatment of the complex containing a nipecotic acid derivative provides a bridged 8-azatricyclo[6.3.1.0 2 ' 6 ]dodecanecarboxylic acid derivative.

Original languageEnglish
Pages (from-to)3396-3407
Number of pages12
JournalOrganometallics
Volume14
Issue number7
DOIs
Publication statusPublished - 1995 Jan 1

Fingerprint

Bearings (structural)
Cyclization
dienes
Carbon Monoxide
musculoskeletal system
amino acids
Nitrogen
Derivatives
Amino Acids
nitrogen
acids
synthesis
Acids
ligands
phenylalanine
Imino Acids
Sarcosine
Ligands
alanine
carbon monoxide

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Diastereoselective Synthesis of Nitrogen-Containing Heterobicyclic and -tricyclic Skeletons via Intramolecular Cyclization of (η 4 -diene)Fe(CO) 3 Complexes Bearing Amino Acid Derivatives . / Yeh, Ming-Chang P.; Chuang, L. W.; Hwu, C. C.; Sheu, J. M.; Row, L. C.

In: Organometallics, Vol. 14, No. 7, 01.01.1995, p. 3396-3407.

Research output: Contribution to journalArticle

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