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Updated: Jun 5, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Intramolecular Anti-Markovnikov Alkene Hydroaminative Cyclization to cis-2,3-Disubstituted Piperidines
Shaoyu Hao1, Lin Tang1, Chaoren Shen1
1Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
Abstract:
Multisubstituted piperidines are prevalent units in pharmaceuticals. Herein, a photodriven anti-Markovnikov hydroaminative cyclization of a (Z)/(E)-isomeric mixture of trisubstituted alkenes using the lactate-derived C2-symmetric arylthiol catalyst was developed for the synthesis of cis-2,3-disubstituted piperidines and azepane in high diastereoselectivity and good yields. The origin of diastereoselectivity and the observed different hydroamination rate of alkene with different configurations were elucidated by the experimental and computational investigation.
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