Visible Light‐Driven Deracemization of Cyclic Sulfonamides by Quinuclidine and Chiral Arylthiol Catalysis

Abstract A photocatalytic system comprising an achiral tertiary amine and a chiral C 2 ‐symmetric arylthiol was developed for the deracemization of various cyclic sulfonamides. This protocol exhibited high yields, good to excellent enantioselectivity, and broad substrate scope. The resulting products can be readily transformed into diverse diarylmethylamines, presenting a viable alternative to metal‐catalyzed asymmetric methods. The reaction pathway involving a relay of non‐enantioselective hydrogen‐atom abstraction (HAA) and enantioselective hydrogen‐atom delivery (HAD).

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Publication Details

Journal
Angewandte Chemie
Published
2025-06-21
DOI
https://doi.org/10.1002/ange.202505719
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.94
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article

Visible Light‐Driven Deracemization of Cyclic Sulfonamides by Quinuclidine and Chiral Arylthiol Catalysis

Chaoren Shen, Lei Dai, Jing Wang, Yanzhong Li et al.
1 citations
Angewandte Chemie
Sulfur-Based Synthesis Techniques
0.94
article

Visible Light‐Driven Deracemization of Cyclic Sulfonamides by Quinuclidine and Chiral Arylthiol Catalysis

Chaoren Shen, Lei Dai, Jing Wang, Yanzhong Li, Kaiwu Dong
article en
1 citations

Abstract

Abstract A photocatalytic system comprising an achiral tertiary amine and a chiral C 2 ‐symmetric arylthiol was developed for the deracemization of various cyclic sulfonamides. This protocol exhibited high yields, good to excellent enantioselectivity, and broad substrate scope. The resulting products can be readily transformed into diverse diarylmethylamines, presenting a viable alternative to metal‐catalyzed asymmetric methods. The reaction pathway involving a relay of non‐enantioselective hydrogen‐atom abstraction (HAA) and enantioselective hydrogen‐atom delivery (HAD).

Angewandte ChemieVol. 137(34)
East China Normal University (CN)
Openalex Percentile: Top 25%
Sulfur-Based Synthesis Techniques
0.94
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