期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 49, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202212846
关键词
Atropisomerism; C-N Bond Formation; Hydrogen Bonds; Organocatalysis; Quinones
资金
- Taishan Scholar Youth Expert Program in Shandong Province [tsqn201909096]
- National Natural Science Foundation of China [21901236]
- Qingdao University
This study reports a new catalyst that successfully catalyzes the enantioselective coupling reaction between quinone esters and anilines, resulting in the formation of N-aryl quinone atropisomers with a unique intramolecular hydrogen bond. This method has the potential to be used for the synthesis of structurally diverse secondary amine atropisomers.
Diarylamines and related scaffolds are ubiquitous atropisomeric chemotypes in biologically active natural products. However, the catalytic asymmetric synthesis of these axially chiral compounds remains largely unexplored. Herein, we report that a BINOL-derived chiral phosphoric acid (CPA) successfully catalyzed the atroposelective coupling of quinone esters and anilines through direct C-N bond formation to afford N-aryl quinone atropisomers with an unprecedented intramolecular N-H-O hydrogen bond within a six-membered ring in good yields and enantioselectivities with the quinone ester as both the electrophile and the oxidant. A gram-scale experiment demonstrated the utility of this synthetic protocol. Moreover, this methodology provides a platform for the synthesis of structurally diverse secondary amine atropisomers by nucleophilic addition.
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