Enantioselective Palladium(II)‐Catalyzed Desymmetrizative Coupling of 7‐Azabenzonorbornadienes with Alkynylanilines-Reference-Cited by-同舟云学术

Enantioselective Palladium(II)‐Catalyzed Desymmetrizative Coupling of 7‐Azabenzonorbornadienes with Alkynylanilines

Published:2023-11-28 Issue:1 Volume:136 Page:
ISSN:0044-8249
Container-title:Angewandte Chemie
language:en
Short-container-title:Angewandte Chemie

Author:

Meng Junjie¹,He Hui²,Liu Qianru¹,Xu Hanhong¹,Huang Huicai³,Ni Shao‐Fei²,Li Zhaodong¹⁴^ORCID

Affiliation:

1. National Key Laboratory of Green Pesticide College of Materials and Energy South China Agricultural University Guangzhou 510641 Guangdong China

2. Department of Chemistry Shantou University Shantou 515063 Guangdong China

3. Key Laboratory of Chinese Medicinal Resource from Lingnan Ministry of Education School of Pharmaceutical Sciences Guangzhou University of Chinese Medicine Guangzhou 510641 Guangdong China

4. National Key Laboratory on Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture School of Pharmacy Nanjing University of Chinese Medicine Nanjing 210023 Jiangsu China

Abstract

AbstractA PdII‐catalyzed, domino enantioselective desymmetrizative coupling of 7‐azabenzonorbornadienes with alkynylanilines is disclosed herein. This operationally simple transformation generates three covalent bonds and two contiguous stereocenters with excellent enantio‐ and diastereo‐selectivity. The resulting functionalized indole‐dihydronaphthalene‐amine conjugates served as an appealing platform to streamline the diversity‐oriented synthesis (DOS) of other valuable enantioenriched compounds. DFT calculations revealed that the two stabilizing non‐covalent interactions contributed to the observed enantioselectivity.

Funder

National Natural Science Foundation of China

Basic and Applied Basic Research Foundation of Guangdong Province

Publisher

Wiley

Subject

General Medicine

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ange.202315092

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