Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

Autor: Aaron H. Shoemaker, Elizabeth A. Foker, Elena P. Uttaro, Sarah K. Beitel, Daniel R. Griffith
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 19, Iss 1, Pp 1615-1619 (2023)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.19.118
Popis: The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron complex, and 3) an intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield.
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