Affiliation:
1. Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and Technology Shenzhen 518055 Guangdong P. R. China
2. State Key Laboratory of Elemento-Organic Chemistry Nankai University 300071 Tianjin P. R. China
Abstract
AbstractEnantioenriched α‐tertiary‐α‐aminoacid and α‐chiral‐β‐aminoacid derivatives play an important role in biological science and pharmaceutical chemistry. Thus, the development of methods for their synthesis is highly valuable and yet remains challenging. Herein, an unprecedented catalyst‐controlled regiodivergent and enantioselective formal hydroamination of N,N‐disubstituted acrylamides with aminating agents has been developed, accessing enantioenriched α‐tertiary‐α‐aminolactam and α‐chiral‐β‐aminoamide derivatives. Sterically‐disfavored and electronically‐disfavored enantioselective hydroamination of electron‐deficient alkenes have been successfully tuned using different transition metals and chiral ligands. Notably, extremely hindered aliphatic α‐tertiary‐α‐aminolactam derivatives were synthesized by Cu−H catalyzed asymmetric C−N bond forming with tertiary alkyl species. Enantioenriched α‐chiral‐β‐aminoamide derivatives have been accessed by Ni−H catalyzed anti‐Markovnikov‐selective formal hydroaminations of alkenes. This set of reactions tolerates a wide range of functional groups to deliver diverse α‐tertiary‐α‐aminolactam and α‐chiral‐β‐aminoamide derivatives in good yields with high levels of enantioselectivity.
Funder
National Natural Science Foundation of China
Natural Science Foundation of Guangdong Province
Department of Education of Guangdong Province
Science, Technology and Innovation Commission of Shenzhen Municipality
Guangdong Science and Technology Department
Subject
General Chemistry,Catalysis
Cited by
6 articles.
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