Dearomatization of 3‐Nitroindoles by a Phosphine‐Catalyzed Enantioselective [3+2] Annulation Reaction

• Published in: Angewandte Chemie International Edition Vol. 58; no. 16; pp. 5427 - 5431
• Main Authors: Li, Kaizhi, Gonçalves, Théo P., Huang, Kuo‐Wei, Lu, Yixin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 08.04.2019; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: [3+2] annulation; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; cyclopentaindolines; dearomatization; Enantiomers; nitroindoles; Organic chemistry; organocatalysis; Phosphine; Physical Sciences; Science & Technology; ASYMMETRIC DEAROMATIZATION; DIELS-ALDER; CRYSTAL-STRUCTURE; dearomatization; 3-ISOTHIOCYANATO OXINDOLES; [3+2] annulation; nitroindoles; INDOLES; CASCADE REACTION; organocatalysis; cyclopentaindolines; CONSTRUCTION; CYCLOADDITION REACTION; DERIVATIVES; ACCESS

The dearomatization of 3‐nitroindoles through a chiral‐phosphine‐mediated [3+2] annulation reaction is described. This method makes use of readily available 3‐nitroindoles as an aromatic feedstock and rapidly delivers a wide range of cyclopentaindoline alkaloid scaffolds in a highly enantioselective...