Iridium-Catalyzed Anti-Stereoselective Ring-Opening Reactions of Azabicyclic Alkenes with Fluoroalkylamines

Wen Yang; Guo Cheng; Yue Li; Xiongjun Zuo; Dingqiao Yang

doi:10.1055/s-0036-1588692

Synthesis, Table of Contents

Synthesis 2017; 49(09): 2025-2034
DOI: 10.1055/s-0036-1588692

paper

Iridium-Catalyzed Anti-Stereoselective Ring-Opening Reactions of Azabicyclic Alkenes with Fluoroalkylamines

Authors

Wen Yang

Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China Email: yangdq@scnu.edu.cn
Guo Cheng

Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China Email: yangdq@scnu.edu.cn
Yue Li

Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China Email: yangdq@scnu.edu.cn
Xiongjun Zuo

Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China Email: yangdq@scnu.edu.cn
Dingqiao Yang*

Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China Email: yangdq@scnu.edu.cn

Abstract

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Abstract

A novel iridium-catalyzed ring-opening reaction of azabicyclic alkenes with a variety of fluoroalkylamines was developed. The reaction gave a series of fluorinated trans-1,2-diamine derivatives in good to excellent yields (up to 98%) under relatively mild conditions. The effects of various ligands, catalyst loading, solvents, and temperatures on the yield of the reaction were also investigated. This is the first time that fluorinated compounds were synthesized by incorporating a series of fluoroalkylamines into hydronaphthalene skeleton.

Key words

iridium catalyst - fluoroalkylamines - azabicyclic alkenes - ring-opening reaction - fluorinated trans-1,2-diamines

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