Chiral Lewis Base/Achiral Acid <scp>Co‐Catalyzed</scp> Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides-Reference-Cited by-同舟云学术

Chiral Lewis Base/Achiral Acid Co‐Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides

Published:2024-04-25 Issue:17 Volume:42 Page:2005-2009
ISSN:1001-604X
Container-title:Chinese Journal of Chemistry
language:en
Short-container-title:Chin. J. Chem.

Author:

Yang Qin¹,Luo Hui‐Yun¹,Zhu Deng¹,Zhang Xin‐Yu¹,Ke Hua²,Chen Zhi‐Min¹³

Affiliation:

1. School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University Shanghai 200240 China

2. Engineering Technology Research Center for Environmental Protection Materials Pingxiang University Pingxiang Jiangxi 337055 China

3. State Key Laboratory of Applied Organic Chemistry Lanzhou University Lanzhou Gansu 730000 China

Abstract

Comprehensive SummaryChiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time. A variety of C—N axially chiral sulfur‐containing pyrrole derivatives were readily obtained in moderate to good yields with moderate to excellent enantioselectivities. This catalytic system involves sequential desymmetrization and kinetic resolution.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Jiangxi Province

Natural Science Foundation of Shanghai Municipality

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/cjoc.202400255

Reference28 articles.

1. Highly efficient stereoconservative syntheses of new, bifunctional atropisomeric organocatalysts

2. The Marinopyrroles, Antibiotics of an Unprecedented Structure Class from a Marine Streptomyces sp.

3. Organocatalytic Atroposelective Synthesis of Indole Derivatives Bearing Axial Chirality: Strategies and Applications

4. Organocatalytic Enantioselective Synthesis of Axially Chiral Molecules: Development of Strategies and Skeletons

5. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds