Cu-Catalyzed Enantioselective S-Arylation of Sulfenamides Enabled by Confined Ligands

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-20 DOI:10.1021/acs.orglett.5c00132

Xiao-Bao Wu, Yue Shen, Hua-Jie Jiang, Liu-Zhu Gong

引用次数: 0

Abstract

Chiral sulfilimines, aza analogues of sulfoxides, are essential in natural products and pharmaceuticals, highlighting the importance of their synthesis in asymmetric catalysis. However, efficient approaches for synthesizing chiral diaryl sulfilimines are still rare and challenging, particularly for those with two sterically similar aryl groups. Herein, we present a mild and efficient protocol for generating diverse enantioenriched diaryl and aryl alkyl sulfilimines via copper-catalyzed enantioselective S-arylation of N-acyl sulfenamides with diaryliodonium salts. A bulky PyBox ligand is crucial for stereocontrol, delivering various sulfilimines with up to 95% ee (51 examples).

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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.