Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles
Summary: Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excelle...
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| Format: | Article |
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Elsevier
2020-02-01
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| Series: | iScience |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2589004220300572 |
| _version_ | 1818014610694864896 |
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| author | Guang-Jian Mei Wenrui Zheng Théo P. Gonçalves Xiwen Tang Kuo-Wei Huang Yixin Lu |
| author_facet | Guang-Jian Mei Wenrui Zheng Théo P. Gonçalves Xiwen Tang Kuo-Wei Huang Yixin Lu |
| author_sort | Guang-Jian Mei |
| collection | DOAJ |
| description | Summary: Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context. : Organic Chemistry; Organic Synthesis; Physical Organic Chemistry Subject Areas: Organic Chemistry, Organic Synthesis, Physical Organic Chemistry |
| first_indexed | 2024-04-14T06:46:28Z |
| format | Article |
| id | doaj.art-55981fc9051e4ea7af82e9e86d7a0c0c |
| institution | Directory Open Access Journal |
| issn | 2589-0042 |
| language | English |
| last_indexed | 2024-04-14T06:46:28Z |
| publishDate | 2020-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | iScience |
| spelling | doaj.art-55981fc9051e4ea7af82e9e86d7a0c0c2022-12-22T02:07:09ZengElsevieriScience2589-00422020-02-01232Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-DihydropyrrolesGuang-Jian Mei0Wenrui Zheng1Théo P. Gonçalves2Xiwen Tang3Kuo-Wei Huang4Yixin Lu5Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, SingaporeKAUST Catalysis Center and Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi ArabiaDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, SingaporeKAUST Catalysis Center and Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi ArabiaDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore; Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, Fujian 359297, PR China; National University of Singapore (Suzhou) Research Institute, 377 Lin Quan Street, Suzhou Industrial Park, Suzhou, 215123, China; Corresponding authorSummary: Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context. : Organic Chemistry; Organic Synthesis; Physical Organic Chemistry Subject Areas: Organic Chemistry, Organic Synthesis, Physical Organic Chemistryhttp://www.sciencedirect.com/science/article/pii/S2589004220300572 |
| spellingShingle | Guang-Jian Mei Wenrui Zheng Théo P. Gonçalves Xiwen Tang Kuo-Wei Huang Yixin Lu Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles iScience |
| title | Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles |
| title_full | Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles |
| title_fullStr | Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles |
| title_full_unstemmed | Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles |
| title_short | Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles |
| title_sort | catalytic asymmetric formal 3 2 cycloaddition of azoalkenes with 3 vinylindoles synthesis of 2 3 dihydropyrroles |
| url | http://www.sciencedirect.com/science/article/pii/S2589004220300572 |
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