Intramolecular Anti-Markovnikov Alkene Hydroaminative Cyclization to cis -2,3-Disubstituted Piperidines

Multisubstituted piperidines are prevalent units in pharmaceuticals. Herein, a photodriven anti-Markovnikov hydroaminative cyclization of a ( )/( )-isomeric mixture of trisubstituted alkenes using the lactate-derived -symmetric arylthiol catalyst was developed for the synthesis of -2,3-disubstituted...

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Published in:Organic letters 2024-12
Main Authors: Hao, Shaoyu, Tang, Lin, Shen, Chaoren, Dong, Kaiwu
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Tang, Lin
Shen, Chaoren
Dong, Kaiwu
description Multisubstituted piperidines are prevalent units in pharmaceuticals. Herein, a photodriven anti-Markovnikov hydroaminative cyclization of a ( )/( )-isomeric mixture of trisubstituted alkenes using the lactate-derived -symmetric arylthiol catalyst was developed for the synthesis of -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.
doi_str_mv 10.1021/acs.orglett.4c04345
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title Intramolecular Anti-Markovnikov Alkene Hydroaminative Cyclization to cis -2,3-Disubstituted Piperidines
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