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Updated: Sep 6, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Cascade Michael/aza-Michael Addition of α-Fluoroacetamides to p-Quinone Monoacetals Enables Monofluorinated Bridged
Mumtaz Ahmad1,2, Durgesh Balodi1, Gurudayal Prajapati3
1Medicinal & Process Chemistry Division and, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow226031, India.
Abstract:
We report a diastereoselective synthesis of monofluorinated bridged azabicyclo[3.3.1]nonanones, a rare class of structurally privileged scaffolds, via a pyrrolidine-catalyzed double Michael addition of α-fluoroacetoacetamides to p-quinone monoacetals. The protocol was further extended to quinone imine ketals, providing access to functionalized fluorine-containing azabicyclo[3.3.1]nonane sulfonamides and α-aryl-α-fluoroacetamides. The method features broad substrate scope, excellent functional-group tolerance, gram-scale applicability, and straightforward derivatization, offering direct access to fluorinated bridged lactam frameworks.
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