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Updated: May 9, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
Chiral Phosphine Oxide-Catalyzed Enantioselective Transannular Bromoaminocyclization for the Synthesis of Tropanes
Wan-Li Zhu1, Zhuo Pan2, Geng Zhang1
1Anhui Province Key Laboratory of Value Added Catalytic Conversion and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China.
Abstract:
A chiral phosphine oxide-catalyzed enantioselective transannular bromoaminocyclization is developed for the enantioselective synthesis of tropane scaffolds. Under optimized conditions, various 5-aminocyclohept-1-enes are converted to 8-azabicyclo[3.2.1]octanes in excellent yields (up to 99%) and enantioselectivities (up to 99% ee). Gram-scale synthesis and derivatization proceed without a loss of stereochemical integrity. DFT calculations support a hydrogen-bonding-controlled mechanism. This strategy provides a concise route to chiral tropane derivatives.
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