Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 16, Pages 5427-5431Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900248
Keywords
[3+2] annulation; cyclopentaindolines; dearomatization; nitroindoles; organocatalysis
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Funding
- Singapore National Research Foundation, Prime Minister's Office [R-143-000-A15-281]
- National University of Singapore [R-143-000-695-114]
- National Natural Science Foundation of China [21672158]
- King Abdullah University of Science and Technology (KAUST)
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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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