Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction
7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita–Baylis–Hillman (MBH) reactions with maleimides using a bifunctiona...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2016-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.12.33 |
| _version_ | 1818873991877623808 |
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| author | Qing He Gu Zhan Wei Du Ying-Chun Chen |
| author_facet | Qing He Gu Zhan Wei Du Ying-Chun Chen |
| author_sort | Qing He |
| collection | DOAJ |
| description | 7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita–Baylis–Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approach to access multifunctional 3-hydroxy-7-aza-2-oxindoles with high enantiopurity (up to 94% ee). Other types of activated alkenes, such as acrylates and acrolein, could also be efficiently utilized. |
| first_indexed | 2024-12-19T13:03:30Z |
| format | Article |
| id | doaj.art-be7b037f8f3c48438229222206ab5dda |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T13:03:30Z |
| publishDate | 2016-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-be7b037f8f3c48438229222206ab5dda2022-12-21T20:20:10ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-02-0112130931310.3762/bjoc.12.331860-5397-12-33Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reactionQing He0Gu Zhan1Wei Du2Ying-Chun Chen3Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, ChinaKey Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, ChinaKey Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, ChinaKey Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita–Baylis–Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approach to access multifunctional 3-hydroxy-7-aza-2-oxindoles with high enantiopurity (up to 94% ee). Other types of activated alkenes, such as acrylates and acrolein, could also be efficiently utilized.https://doi.org/10.3762/bjoc.12.337-azaisatinsβ-isocupreidinebifunctional catalysismaleimideMBH reaction |
| spellingShingle | Qing He Gu Zhan Wei Du Ying-Chun Chen Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction Beilstein Journal of Organic Chemistry 7-azaisatins β-isocupreidine bifunctional catalysis maleimide MBH reaction |
| title | Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction |
| title_full | Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction |
| title_fullStr | Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction |
| title_full_unstemmed | Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction |
| title_short | Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction |
| title_sort | application of 7 azaisatins in enantioselective morita baylis hillman reaction |
| topic | 7-azaisatins β-isocupreidine bifunctional catalysis maleimide MBH reaction |
| url | https://doi.org/10.3762/bjoc.12.33 |
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