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

Kaizhi Li; Théo P Gonçalves; Kuo-Wei Huang; Yixin Lu

doi:10.1002/anie.201900248

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

Angew Chem Int Ed Engl. 2019 Apr 8;58(16):5427-5431. doi: 10.1002/anie.201900248. Epub 2019 Mar 14.

Authors

Kaizhi Li¹, Théo P Gonçalves², Kuo-Wei Huang², Yixin Lu^{1

3}

Affiliations

¹ Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore.
² KAUST Catalysis Center and Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal, 23955-6900, Saudi Arabia.
³ National University of Singapore (Suzhou) Research Institute, 377 Lin Quan Street, Suzhou Industrial Park, Suzhou, Jiangsu, 215123, P. R. China.

PMID: 30770616
DOI: 10.1002/anie.201900248

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.

Keywords: [3+2] annulation; cyclopentaindolines; dearomatization; nitroindoles; organocatalysis.

Publication types

Research Support, Non-U.S. Gov't

Abstract

Publication types

Grants and funding