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

Abstract
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.

Beilstein J. Org. Chem. 2023, 19, 1615–1619. doi:10.3762/bjoc.19.118

Source: Beilstein Journal of Organic Chemistry - October 23, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: alkaloids azabicycles Heck reaction iron complex tropone Full Research Paper Source Type: research