Alkylative Ring-Opening of Bicyclic Aziridinium Ion and Its Application for Alkaloid Synthesis
Alkylative ring-opening of bicyclic aziridinium ion generated from 4-hydroxybutylaziridine with organocopper reagent was achieved successfully to afford 2-alkylsubstituted piperidine in high or moderate yield. This method allowed carbon-carbon bond formation of “non-activated” aziridine via aziridin...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2019-06-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00460/full |
| _version_ | 1811323020012158976 |
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| author | Nagendra Nath Yadav Young-Gun Lee Nikhil Srivastava Hyun-Joon Ha |
| author_facet | Nagendra Nath Yadav Young-Gun Lee Nikhil Srivastava Hyun-Joon Ha |
| author_sort | Nagendra Nath Yadav |
| collection | DOAJ |
| description | Alkylative ring-opening of bicyclic aziridinium ion generated from 4-hydroxybutylaziridine with organocopper reagent was achieved successfully to afford 2-alkylsubstituted piperidine in high or moderate yield. This method allowed carbon-carbon bond formation of “non-activated” aziridine via aziridinium ion ring-opening in regio- and stereo-selective manner for the first time. This newly developed reaction was applied for an efficient synthesis of alkaloid with the representative example of conine and epiquinamide. |
| first_indexed | 2024-04-13T13:46:39Z |
| format | Article |
| id | doaj.art-5dc07021c5c04edfb74a038bdec27db1 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-13T13:46:39Z |
| publishDate | 2019-06-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-5dc07021c5c04edfb74a038bdec27db12022-12-22T02:44:28ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-06-01710.3389/fchem.2019.00460470026Alkylative Ring-Opening of Bicyclic Aziridinium Ion and Its Application for Alkaloid SynthesisNagendra Nath Yadav0Young-Gun Lee1Nikhil Srivastava2Hyun-Joon Ha3Department of Chemistry, North Eastern Regional Institute of Science and Technology, Nirjuli, IndiaDepartment of Chemistry, Hankuk University of Foreign Studies, Yongin, South KoreaDepartment of Chemistry, Hankuk University of Foreign Studies, Yongin, South KoreaDepartment of Chemistry, Hankuk University of Foreign Studies, Yongin, South KoreaAlkylative ring-opening of bicyclic aziridinium ion generated from 4-hydroxybutylaziridine with organocopper reagent was achieved successfully to afford 2-alkylsubstituted piperidine in high or moderate yield. This method allowed carbon-carbon bond formation of “non-activated” aziridine via aziridinium ion ring-opening in regio- and stereo-selective manner for the first time. This newly developed reaction was applied for an efficient synthesis of alkaloid with the representative example of conine and epiquinamide.https://www.frontiersin.org/article/10.3389/fchem.2019.00460/fullaziridinebicyclic aziridinium ionsalkylationring-expansionalkaloid synthesis |
| spellingShingle | Nagendra Nath Yadav Young-Gun Lee Nikhil Srivastava Hyun-Joon Ha Alkylative Ring-Opening of Bicyclic Aziridinium Ion and Its Application for Alkaloid Synthesis Frontiers in Chemistry aziridine bicyclic aziridinium ions alkylation ring-expansion alkaloid synthesis |
| title | Alkylative Ring-Opening of Bicyclic Aziridinium Ion and Its Application for Alkaloid Synthesis |
| title_full | Alkylative Ring-Opening of Bicyclic Aziridinium Ion and Its Application for Alkaloid Synthesis |
| title_fullStr | Alkylative Ring-Opening of Bicyclic Aziridinium Ion and Its Application for Alkaloid Synthesis |
| title_full_unstemmed | Alkylative Ring-Opening of Bicyclic Aziridinium Ion and Its Application for Alkaloid Synthesis |
| title_short | Alkylative Ring-Opening of Bicyclic Aziridinium Ion and Its Application for Alkaloid Synthesis |
| title_sort | alkylative ring opening of bicyclic aziridinium ion and its application for alkaloid synthesis |
| topic | aziridine bicyclic aziridinium ions alkylation ring-expansion alkaloid synthesis |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00460/full |
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