阿托品
对映选择合成
外消旋化
化学
吡咯
组合化学
催化作用
轴手性
酰胺
立体化学
有机化学
作者
Yuanlin Wei,Fei Sun,Guofeng Li,Shiyu Xu,Ming Zhang,Hong Liu
标识
DOI:10.1021/acs.orglett.3c03280
摘要
The catalytic asymmetric construction of monoheteroaryl N-N axially chiral compounds and chiral five-membered aryl-based scaffolds remains challenging. Herein, we present a highly efficient enantioselective synthesis of monoheteroaryl N-N atropisomers via an asymmetric Paal-Knorr reaction, affording a diverse array of N-N amide-pyrrole atropisomers with excellent enantioselectivities. Gram-scale synthesis and post-transformations of the product demonstrated the synthesis utility of this method. Racemization experiments confirmed the configurational stability of these N-N axially chiral products. This study not only provides the first de novo cyclization example for accessing an asymmetric monoheteroaryl N-N scaffold but also offers a new member of the N-N atropisomer family with potential synthetic and medicinal applications.
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