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Asymmetric Synthesis of Hydroquinolines with α,α‐Disubstitution through Organocatalyzed Kinetic Resolution
Author(s) -
Chen Yunrong,
Zhu Chaofan,
Guo Zheng,
Liu Wei,
Yang Xiaoyu
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202015008
Subject(s) - kinetic resolution , chemistry , electrophile , moiety , substrate (aquarium) , catalysis , enantioselective synthesis , organocatalysis , combinatorial chemistry , phosphoric acid , hydrazine (antidepressant) , organic chemistry , oceanography , geology , chromatography
The first kinetic resolution of hydroquinoline derivatives with α,α‐disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate‐ and enantio‐determining electrophilic attack promoted by a network of attractive non‐covalent interactions between the substrate and catalyst. Facile subsequent removal and transformations of the newly introduced hydrazine moiety enable these protocols to serve as powerful tools for asymmetric synthesis of N‐heterocycles with α,α‐disubstitution.