Affiliation:
1. Shenzhen Key Laboratory of Cross-Coupling Reactions Southern University of Science and Technology Shenzhen 518055 China
2. Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and Technology Shenzhen 518055 China
3. Academy for Advanced Interdisciplinary Studies and Department of Chemistry Southern University of Science and Technology Shenzhen 518055 China
Abstract
AbstractTransition‐metal catalyzed enantioconvergent cross‐coupling of tertiary alkyl halides with ammonia offers a rapid avenue to chiral unnatural α,α‐disubstituted amino acids. However, the construction of chiral C−N bonds between tertiary‐carbon electrophiles and nitrogen nucleophiles presented a great challenge owing to steric congestion. We report a copper‐catalyzed enantioconvergent radical C−N cross‐coupling of alkyl halides with sulfoximines (as ammonia surrogates) under mild conditions by employing a chiral anionic N,N,N‐ligand with a long spreading side arm. An array of α,α‐disubstituted amino acid derivatives were obtained with good efficiency and enantioselectivity. The synthetic utility of the strategy has been showcased by the elaboration of the coupling products into different chiral α‐fully substituted amine building blocks.
Funder
National Key Research and Development Program of China
National Natural Science Foundation of China
Basic and Applied Basic Research Foundation of Guangdong Province