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[6.3.0.02'6]undecane and 7-azatricyclo[7.3.0.02'7]dodecane ring systems, respectively, whereas treatment of the complex containing a nipecotic acid derivative provides a bridged 8-azatricyclo[6.3.1.02'6]dodecanecarboxylic acid derivative.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry