分子内反马尔科夫尼科夫烯烃氢化氨基环化成顺式-2,3-二取代哌啶类化合物

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-16 DOI:10.1021/acs.orglett.4c04345

Shaoyu Hao, Lin Tang, Chaoren Shen, Kaiwu Dong

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摘要

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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

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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 (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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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.