Atroposelective synthesis of N-N axially chiral pyrrolylamides by combined-acid catalytic Paal-Knorr reaction

被引：0
|
作者：
Chen, Zhihuang [1 ]
Chen, Qi [1 ]
Tu, Guogang [1 ]
Xiong, Xiaodong [1 ]
机构：
[1] Nanchang Univ, Sch Pharm, Nanchang 330006, Jiangxi, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2025年 / 61卷 / 26期
基金：
中国国家自然科学基金;
关键词：
PYRROLES;
D O I：
10.1039/d4cc06721e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A general and efficient method for the construction of enantiomerically pure N-N axially chiral pyrrolylamides by utilizing the catalytic asymmetric Paal-Knorr reaction has been developed. The key to success is the use of the binary-acid catalytic system involving the dramatic synergistic effect of a Lewis acid and a chiral phosphoric acid for achieving effective stereocontrol.
引用
收藏
页码：5007 / 5010
页数：4
相关论文
共 50 条
  • [31] Reversion of Paal-Knorr synthesis:: A new strategy for ring-opening and N-substituent change in 1H-pyrroles
    Zamora, Rosario
    Hidalgo, Francisco J.
    SYNLETT, 2006, (09) : 1428 - 1430
  • [32] Asymmetric Synthesis of Axially Chiral Anilides via Organocatalytic Atroposelective N-Acylation
    Li, Dawei
    Wang, Sijing
    Ge, Shulin
    Dong, Shunxi
    Feng, Xiaoming
    ORGANIC LETTERS, 2020, 22 (14) : 5331 - 5336
  • [33] Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach
    Dittrich, Nora
    Pilkington, Lisa I.
    Leung, Euphemia
    Barker, David
    TETRAHEDRON, 2017, 73 (14) : 1881 - 1894
  • [34] Asymmetric Synthesis of N-N Axially Chiral Compounds by Phase-Transfer-Catalyzed Alkylations
    Pan, Ming
    Shao, Ying-Bo
    Zhao, Qun
    Li, Xin
    ORGANIC LETTERS, 2022, 24 (01) : 374 - 378
  • [35] Ascorbic acid as a multifunctional hydrogen bonding catalyst for Paal-Knorr synthesis of N-substituted mono- and bis-pyrroles: experimental and theoretical aspects
    Ghaemi, Amin
    Darabi, Hossein Reza
    Aghapoor, Kioumars
    Mohsenzadeh, Farshid
    Sayahi, Hani
    Taherzadeh, Hossein
    Mojdehi, Maryam Farajpour
    Balavar, Yadollah
    Farhangian, Hossein
    RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (09) : 4087 - 4102
  • [36] Pd-catalyzed asymmetric Larock reaction for the atroposelective synthesis of N―N chiral indoles
    Wang, Jinlei
    Pan, Deng
    Wang, Fen
    Yu, Songjie
    Huang, Genping
    Li, Xingwei
    SCIENCE ADVANCES, 2024, 10 (19):
  • [37] Synthesis of Axially Chiral N-Arylindoles via Atroposelective Cyclization of Ynamides Catalyzed by Chiral Bronsted Acids
    Wang, Ze-Shu
    Zhu, Lu-Jing
    Li, Cui-Ting
    Liu, Bin-Yang
    Hong, Xin
    Ye, Long-Wu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (20)
  • [38] Biocatalytic Atroposelective Synthesis of Axially Chiral N-Arylindoles via Dynamic Kinetic Resolution
    Rodriguez-Salamanca, Patricia
    de Gonzalo, Gonzalo
    Carmona, Jose A.
    Lopez-Serrano, Joaquin
    Iglesias-Siguenza, Javier
    Fernandez, Rosario
    Lassaletta, Jose M.
    Hornillos, Valentin
    ACS CATALYSIS, 2023, 13 (01) : 659 - 664
  • [39] Catalytic atroposelective synthesis of heterobiaryls with vicinal C-C and N-N diaxes via dynamic kinetic resolution
    Han, Tian-Jiao
    Guan, Chun-Yan
    Li, Na
    Dong, Rui
    Xu, Li-Ping
    Xiao, Xiao
    Wang, Min-Can
    Mei, Guang-Jian
    ISCIENCE, 2023, 26 (10)
  • [40] N-Heterocyclic Carbene Control over Multiple Stereogenicities: Atroposelective Synthesis of Axially Chiral Phthalimides
    Barday, Manuel
    Rodrigues, Jessica
    Bouillac, Pierre
    Rodriguez, Jean
    Amatore, Muriel
    Constantieux, Thierry
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (02) : 148 - 155
12345