Dearomatization of 3‐Nitroindoles by a Phosphine‐Catalyzed Enantioselective [3+2] Annulation Reaction. Issue 16 (14th March 2019)

• Record Type: Journal Article
• Authors: Li, Kaizhi; Gonçalves, Théo P.; Huang, Kuo‐Wei; Lu, Yixin
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 16(2019)
• Page Start: 5427
• Page End: 5431
• Publication Date: 2019-03-14
• Subjects: [3+2] annulation -- cyclopentaindolines -- dearomatization -- nitroindoles -- organocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201900248
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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 manner. Notably, phosphine‐triggered cyclization has not been utilized previously in a dearomatization process. Abstract : A disruptive influence : Variously substituted 3‐nitroindoles underwent dearomatization in a phosphine‐catalyzed asymmetric [3+2] annulation reaction with allenoates (see scheme). This method makes use of 3‐nitroindoles as a readily available aromatic feedstock and provides access to a wide range of cyclopentaindolines in a highly enantioselective manner.