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

Kaizhi Li; Theo Goncalves; Kuo-Wei Huang; Yixin Lu

doi:10.1002/anie.201900248

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

Kaizhi Li, Theo Goncalves, Kuo-Wei Huang, Yixin Lu

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104 Scopus citations

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.

Original language	English (US)
Pages (from-to)	5427-5431
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	58
Issue number	16
DOIs	https://doi.org/10.1002/anie.201900248 https://doi.org/10.1002/ange.201900248
State	Published - Mar 14 2019

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

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.",

author = "Kaizhi Li and Theo Goncalves and Kuo-Wei Huang and Yixin Lu",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Y.L. thanks the Singapore National Research Foundation, Prime Minister's Office for the NRF Investigatorship Award (R-143-000-A15-281). Financial support from the National University of Singapore (R-143-000-695-114) and the National Natural Science Foundation of China (21672158) is also gratefully acknowledged. The service of Ibex, Shaheen 2 High Performance Computing Facilities was provided to K.-W. H. with financial support from King Abdullah University of Science and Technology (KAUST).",

year = "2019",

month = mar,

day = "14",

doi = "10.1002/anie.201900248",

language = "English (US)",

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journal = "Angewandte Chemie International Edition",

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AU - Li, Kaizhi

AU - Goncalves, Theo

AU - Huang, Kuo-Wei

AU - Lu, Yixin

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Y.L. thanks the Singapore National Research Foundation, Prime Minister's Office for the NRF Investigatorship Award (R-143-000-A15-281). Financial support from the National University of Singapore (R-143-000-695-114) and the National Natural Science Foundation of China (21672158) is also gratefully acknowledged. The service of Ibex, Shaheen 2 High Performance Computing Facilities was provided to K.-W. H. with financial support from King Abdullah University of Science and Technology (KAUST).

PY - 2019/3/14

Y1 - 2019/3/14

N2 - 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.

AB - 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.

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

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CCDC 1858193: Experimental Crystal Structure Determination : 4-t-butyl 3-(9H-fluoren-9-yl) 7-bromo-8b-nitro-3a,8b-dihydrocyclopenta[b]indole-3,4(1H)-dicarboxylate

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

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CCDC 1858193: Experimental Crystal Structure Determination : 4-t-butyl 3-(9H-fluoren-9-yl) 7-bromo-8b-nitro-3a,8b-dihydrocyclopenta[b]indole-3,4(1H)-dicarboxylate

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