Visible-Light-Mediated, Diastereoselective Epimerization of Exocyclic Amines,Organic Letters

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Visible-Light-Mediated, Diastereoselective Epimerization of Exocyclic Amines
Organic Letters ( IF 4.9 ) Pub Date : 2023-12-19 , DOI: 10.1021/acs.orglett.3c03801
María A Vargas-Rivera ₁ , Aidan S Liu ₁ , Jonathan A Ellman ₁

Affiliation

Stereoselective α-amino C–H epimerization of exocyclic amines is achieved via photoredox catalyzed, thiyl-radical mediated, reversible hydrogen atom transfer to provide thermodynamically controlled anti/syn isomer ratios. The method is applicable to different substituents and substitution patterns about aminocyclopentanes, aminocyclohexanes, and a N-Boc-3-aminopiperidine. The method also provided efficient epimerization for primary, alkyl and (hetero)aryl secondary, and tertiary exocyclic amines. Demonstration of reversible epimerization, deuterium labeling, and luminescence quenching provides insight into the reaction mechanism.

中文翻译：

可见光介导的外环胺的非对映选择性差向异构化

外环胺的立体选择性 α-氨基 C-H 差向异构化是通过光氧化还原催化的、巯基自由基介导的可逆氢原子转移来实现的，以提供热力学控制的抗/syn 异构体比率。该方法适用于氨基环戊烷、氨基环己烷和 N-Boc-3-氨基哌啶的不同取代基和取代模式。该方法还为伯、烷基和（杂）芳基仲胺和叔外环胺提供了高效的差向异构化。可逆差向异构化、氘标记和发光淬灭的演示为反应机理提供了见解。

更新日期：2023-12-19

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