Chiral Phosphoric Acid Catalyzed Enantioselective Desymmetrization of 1,4-Dihydropyridines by C(sp3)-H Bromination

被引：11

作者：

Han, Min ^{[1
,2
]}

Zhang, Shi-qi ^{[1
]}

Cui, Xin ^{[1
]}

Wang, Qi-wei ^{[2
,3
]}

Li, Guang-xun ^{[1
]}

Tang, Zhuo ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Sichuan, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Sichuan, Peoples R China

[3] Xihua Univ, Dept Chem, Chengdu 610039, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 22期

基金：

中国科学院西部之光基金;

关键词：

1; 4-Dihydropyridines; Axial Chirality; Bromination; Desymmetrization; Organocatalysis; ASYMMETRIC-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; KINETIC RESOLUTION; BAY K-8644; CONVERSION; DIHYDROPYRIDINES; CYCLIZATION; OXIDATION; AGONIST; ACCESS;

D O I：

10.1002/anie.202201418

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Described herein is the enantioselective synthesis of Hantzsch-type 1,4-dihydropyridines (DHPs), which are frequently contained in pharmaceuticals. Readily available symmetrical 1,4-DHPs were used as substrates, and the methyl group at the 2- or 6-position of the 1,4-DHP was selectively monobrominated by desymmetrizing enantioselective bromination. The inert C-H bond was converted into a versatile C-Br bond, which guaranteed the modification of the chiral 1,4-DHP derivatives with high efficiency. Furthermore, axially chiral 4-aryl pyridines were accessible by central-to-axial chirality conversion.

引用

页数：6

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