Copper‐Catalyzed Azide–Ynamide Cyclization to Generate α‐Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N‐Heterocycles

• Published in: Angewandte Chemie International Edition Vol. 59; no. 41; pp. 17984 - 17990
• Main Authors: Liu, Xin, Wang, Ze‐Shu, Zhai, Tong‐Yi, Luo, Chen, Zhang, Yi‐Ping, Chen, Yang‐Bo, Deng, Chao, Liu, Rai‐Shung, Ye, Long‐Wu
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 05.10.2020; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Alkynes; asymmetric catalysis; Asymmetry; Carbenes; Catalysts; Chemistry; Chemistry, Multidisciplinary; Copper; cyclizations; Divergence; Enantiomers; heterocycles; Intermediates; Physical Sciences; Science & Technology; Substrates; 2H-AZIRINES; TETHERED ALKYNES; C-H ANNULATION; alkynes; EFFICIENT SYNTHESIS; RAPID ACCESS; asymmetric catalysis; 2-ALKYNYL ARYLAZIDES; CASCADE REACTION; NUCLEOPHILIC NITRENOIDS; cyclizations; CYCLOADDITION; heterocycles; copper; OXO GOLD CARBENES

Here an efficient copper‐catalyzed cascade cyclization of azide‐ynamides via α‐imino copper carbene intermediates is reported, representing the first generation of α‐imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N‐heterocycl...