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Updated: Jun 10, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis of Dioxo-Azabicyclo[3.2.1]octanes via Hypervalent Iodine-Mediated Domino Reaction
Jingjing Chen1, Yu Jin1, Jialing Fu1
1Jiangsu Key Laboratory of Drug Design and Optimization, Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 210009, China.
Abstract:
Bicyclo[3.2.1]octane (BCO) skeleton widely exists in natural products and biologically active molecules, whereas the development of convenient approaches to construct this structure remains a challenge. Herein, we describe a cascade reaction to synthesize 6,8-dioxa-3-azabicycle[3.2.1]octane derivatives from β-keto allylamines via an oxidation-cyclization reaction. A series of dioxo-azabicyclo[3.2.1]octanes bearing a quaternary carbon center were obtained in good yields under mild reaction conditions. Moreover, the mechanistic rationale for this novel domino reaction is supported by control experiments.
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