Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] Derivatives
With a dinuclear zinc-ProPhenol complex as a catalyst, an efficient and novel [3 + 3] annulation of indoline-2-thiones and isatylidene malononitriles has been successfully developed via the Brønsted base and Lewis acid cooperative activation model. This practical methodology gives access to a broad...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-01-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/3/1056 |
| _version_ | 1797623761312153600 |
|---|---|
| author | Tian-Tian Liu Yu Chen Guang-Jian Mei Yuan-Zhao Hua Shi-Kun Jia Min-Can Wang |
| author_facet | Tian-Tian Liu Yu Chen Guang-Jian Mei Yuan-Zhao Hua Shi-Kun Jia Min-Can Wang |
| author_sort | Tian-Tian Liu |
| collection | DOAJ |
| description | With a dinuclear zinc-ProPhenol complex as a catalyst, an efficient and novel [3 + 3] annulation of indoline-2-thiones and isatylidene malononitriles has been successfully developed via the Brønsted base and Lewis acid cooperative activation model. This practical methodology gives access to a broad range of chiral spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] derivatives in good yields with excellent levels of enantioselectivities (up to 88% yield and 99% ee). |
| first_indexed | 2024-03-11T09:33:20Z |
| format | Article |
| id | doaj.art-5ea6a6592fa84cd3be0eb0677c6d6a3d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T09:33:20Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5ea6a6592fa84cd3be0eb0677c6d6a3d2023-11-16T17:27:02ZengMDPI AGMolecules1420-30492023-01-01283105610.3390/molecules28031056Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] DerivativesTian-Tian Liu0Yu Chen1Guang-Jian Mei2Yuan-Zhao Hua3Shi-Kun Jia4Min-Can Wang5Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaWith a dinuclear zinc-ProPhenol complex as a catalyst, an efficient and novel [3 + 3] annulation of indoline-2-thiones and isatylidene malononitriles has been successfully developed via the Brønsted base and Lewis acid cooperative activation model. This practical methodology gives access to a broad range of chiral spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] derivatives in good yields with excellent levels of enantioselectivities (up to 88% yield and 99% ee).https://www.mdpi.com/1420-3049/28/3/1056dinuclear zinc catalystasymmetric catalytic reaction[3 + 3] annulationindoline-2-thioneisatylidene malononitrile |
| spellingShingle | Tian-Tian Liu Yu Chen Guang-Jian Mei Yuan-Zhao Hua Shi-Kun Jia Min-Can Wang Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] Derivatives Molecules dinuclear zinc catalyst asymmetric catalytic reaction [3 + 3] annulation indoline-2-thione isatylidene malononitrile |
| title | Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] Derivatives |
| title_full | Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] Derivatives |
| title_fullStr | Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] Derivatives |
| title_full_unstemmed | Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] Derivatives |
| title_short | Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-<i>b</i>]indole] Derivatives |
| title_sort | zinc catalyzed enantioselective 3 3 annulation for synthesis of chiral spiro indoline 3 4 thiopyrano 2 3 i b i indole derivatives |
| topic | dinuclear zinc catalyst asymmetric catalytic reaction [3 + 3] annulation indoline-2-thione isatylidene malononitrile |
| url | https://www.mdpi.com/1420-3049/28/3/1056 |
| work_keys_str_mv | AT tiantianliu zinccatalyzedenantioselective33annulationforsynthesisofchiralspiroindoline34thiopyrano23ibiindolederivatives AT yuchen zinccatalyzedenantioselective33annulationforsynthesisofchiralspiroindoline34thiopyrano23ibiindolederivatives AT guangjianmei zinccatalyzedenantioselective33annulationforsynthesisofchiralspiroindoline34thiopyrano23ibiindolederivatives AT yuanzhaohua zinccatalyzedenantioselective33annulationforsynthesisofchiralspiroindoline34thiopyrano23ibiindolederivatives AT shikunjia zinccatalyzedenantioselective33annulationforsynthesisofchiralspiroindoline34thiopyrano23ibiindolederivatives AT mincanwang zinccatalyzedenantioselective33annulationforsynthesisofchiralspiroindoline34thiopyrano23ibiindolederivatives |