Dearomatization of 3‐Nitroindoles by a Phosphine‐Catalyzed Enantioselective [3+2] Annulation Reaction
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...
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| Published in | Angewandte Chemie Vol. 131; no. 16; pp. 5481 - 5485 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
Wiley Subscription Services, Inc
08.04.2019
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| 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.
Ein störender Einfluss: Substituierte 3‐Nitroindole wurden in einer phosphinkatalysierten asymmetrischen [3+2]‐Anellierung mit Allenoaten dearomatisiert (siehe Schema). Das Verfahren nutzt 3‐Nitroindole als leicht verfügbare aromatische Rohstoffe und ermöglicht den Zugang zu einem breiten Spektrum von Cyclopentaindolinen auf hoch enantioselektive Weise. |
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| AbstractList | 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.
Ein störender Einfluss: Substituierte 3‐Nitroindole wurden in einer phosphinkatalysierten asymmetrischen [3+2]‐Anellierung mit Allenoaten dearomatisiert (siehe Schema). Das Verfahren nutzt 3‐Nitroindole als leicht verfügbare aromatische Rohstoffe und ermöglicht den Zugang zu einem breiten Spektrum von Cyclopentaindolinen auf hoch enantioselektive Weise. 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 | Huang, Kuo‐Wei Gonçalves, Théo P. Li, Kaizhi Lu, Yixin |
| Author_xml | – sequence: 1 givenname: Kaizhi surname: Li fullname: Li, Kaizhi organization: National University of Singapore – sequence: 2 givenname: Théo P. surname: Gonçalves fullname: Gonçalves, Théo P. organization: King Abdullah University of Science and Technology – sequence: 3 givenname: Kuo‐Wei surname: Huang fullname: Huang, Kuo‐Wei organization: King Abdullah University of Science and Technology – sequence: 4 givenname: Yixin orcidid: 0000-0002-5730-166X surname: Lu fullname: Lu, Yixin email: chmlyx@nus.edu.sg organization: National University of Singapore (Suzhou) Research Institute |
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| Snippet | The dearomatization of 3‐nitroindoles through a chiral‐phosphine‐mediated [3+2] annulation reaction is described. This method makes use of readily available... |
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| SubjectTerms | [3+2]-Anellierung Chemical reactions Chemistry Cyclopentaindoline Dearomatisierung Enantiomers Nitroindole Organic chemistry Organokatalyse Phosphine |
| Title | Dearomatization of 3‐Nitroindoles by a Phosphine‐Catalyzed Enantioselective [3+2] Annulation Reaction |
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