Atroposelective Electrophilic Sulfenylation of N-Aryl Aminoquinone Derivatives Catalyzed by Chiral SPINOL-Derived Sulfide,Angewandte Chemie International Edition

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Atroposelective Electrophilic Sulfenylation of N-Aryl Aminoquinone Derivatives Catalyzed by Chiral SPINOL-Derived Sulfide
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2022-08-30 , DOI: 10.1002/anie.202211782
Deng Zhu ₁ , Lu Yu _{2,

3} , Hui-Yun Luo ₁ , Xiao-Song Xue _{3,

4} , Zhi-Min Chen ₁

Affiliation

Atroposelective electrophilic sulfenylation of N-aryl aminoquinone derivatives catalyzed by a new chiral SPINOL-derived sulfide has been achieved. Axially chiral sulfur-containing diarylamine derivatives were obtained in moderate to excellent yields with moderate to excellent enantioselectivities. The intramolecular N−H⋅⋅⋅S hydrogen bond is a key parameter for the stability of the C−N axis. DFT calculations revealed the origin of atroposelectivity.

中文翻译：

手性 SPINOL 衍生硫化物催化 N-芳基氨基醌衍生物的阻转选择性亲电磺酰化

已经实现了由新型手性 SPINOL 衍生的硫化物催化的N-芳基氨基醌衍生物的阻转选择性亲电亚磺酰化。轴向手性含硫二芳基胺衍生物以中等至优异的产率获得，具有中等至优异的对映选择性。分子内 N−H····S 氢键是 C−N 轴稳定性的关键参数。DFT 计算揭示了回旋选择性的起源。

更新日期：2022-08-30

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