(Dynamic) Kinetic Resolution of Enamines/Imines: Enantioselective N‐Heterocyclic Carbene Catalyzed [3+3] Annulation of Bromoenals and Enamines/Imines

• Published in: Angewandte Chemie International Edition Vol. 58; no. 4; pp. 1183 - 1187
• Main Authors: Chen, Kun‐Quan, Gao, Zhong‐Hua, Ye, Song
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 21.01.2019; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: annulations; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Enantiomers; heterocycles; Imines; kinetic resolution; N-heterocyclic carbene; Organic chemistry; organocatalysis; Physical Sciences; Science & Technology; N-heterocyclic carbene; ASYMMETRIC TRANSFER HYDROGENATION; ACTIVATION; 2-BROMOENALS; 1,3-DICARBONYL COMPOUNDS; RECEPTOR; ALKYNYL ALDEHYDES; organocatalysis; REARRANGEMENT; annulations; heterocycles; DIHYDROPYRIDINONES; ESTERS; kinetic resolution; STEREOSELECTIVE-SYNTHESIS
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201813047

The enantioselective N‐heterocyclic carbene catalyzed [3+3] annulation of α‐bromoenals by dynamic kinetic resolution (DKR) of enamines and normal resolution of α,α‐disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo‐ and enantioselectivities, and a high selective factor (up to 83) was realized for the resolution of α,α‐disubstituted imines. The S factor: The enantioselective N‐heterocyclic carbene (NHC) catalyzed [3+3] annulation of α‐bromoenals by dynamic kinetic resolution (DKR) of enamines, and normal resolution of α,α‐disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo‐ and enantioselectivities, and a high selectivity factor was realized for the resolution of α,α‐disubstituted imines.