Asymmetric Three‐Component Heck Arylation/Amination of Nonconjugated Cyclodienes

D Zhu, Z Jiao, YR Chi, TP Goncalves… - Angewandte Chemie …, 2020 - Wiley Online Library
D Zhu, Z Jiao, YR Chi, TP Goncalves, KW Huang, JS Zhou
Angewandte Chemie International Edition, 2020Wiley Online Library
Substituted cyclohexylamines are becoming increasingly important in drug discovery.
Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5‐aryl
cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary
and secondary anilines, indoline, and benzylamines are suitable amines. The weakly
donating diphosphite Kelliphite forms a deep unsymmetrical pocket, which is essential for
stereoselective anti attack of amines.
Abstract
Substituted cyclohexylamines are becoming increasingly important in drug discovery. Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5‐aryl cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary and secondary anilines, indoline, and benzylamines are suitable amines. The weakly donating diphosphite Kelliphite forms a deep unsymmetrical pocket, which is essential for stereoselective anti attack of amines.
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