Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon ce...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.216 |
| _version_ | 1818447654610272256 |
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| author | Lin Yan Zhiqiang Han Bo Zhu Caiyun Yang Choon-Hong Tan Zhiyong Jiang |
| author_facet | Lin Yan Zhiqiang Han Bo Zhu Caiyun Yang Choon-Hong Tan Zhiyong Jiang |
| author_sort | Lin Yan |
| collection | DOAJ |
| description | In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr). |
| first_indexed | 2024-12-14T20:07:03Z |
| format | Article |
| id | doaj.art-4f052ca1d80d468db6e00fc52bc8fcae |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T20:07:03Z |
| publishDate | 2013-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-4f052ca1d80d468db6e00fc52bc8fcae2022-12-21T22:49:01ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-09-01911853185710.3762/bjoc.9.2161860-5397-9-216Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto estersLin Yan0Zhiqiang Han1Bo Zhu2Caiyun Yang3Choon-Hong Tan4Zhiyong Jiang5Institute of Chemical Biology, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P. R. ChinaInstitute of Chemical Biology, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P. R. ChinaInstitute of Chemical Biology, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P. R. ChinaInstitute of Chemical Biology, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P. R. ChinaKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, P. R. ChinaInstitute of Chemical Biology, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P. R. ChinaIn the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).https://doi.org/10.3762/bjoc.9.216allylic alkylationasymmetric catalysisfluorinefluoro-β-keto estersMorita–Baylis–Hillman carbonatesnatural product |
| spellingShingle | Lin Yan Zhiqiang Han Bo Zhu Caiyun Yang Choon-Hong Tan Zhiyong Jiang Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters Beilstein Journal of Organic Chemistry allylic alkylation asymmetric catalysis fluorine fluoro-β-keto esters Morita–Baylis–Hillman carbonates natural product |
| title | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
| title_full | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
| title_fullStr | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
| title_full_unstemmed | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
| title_short | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
| title_sort | asymmetric allylic alkylation of morita baylis hillman carbonates with α fluoro β keto esters |
| topic | allylic alkylation asymmetric catalysis fluorine fluoro-β-keto esters Morita–Baylis–Hillman carbonates natural product |
| url | https://doi.org/10.3762/bjoc.9.216 |
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