Nickel(II)‐Catalyzed Diastereo‐ and Enantioselective Michael/ Hemiacetalization Cascade Reaction of α‐Ketoesters with 2‐(2‐Nitrovinyl)phenols
A nickel(II)/diamine‐catalyzed diastereo‐ and enantioselective Michael/hemiacetalization cascade reaction of α‐ketoesters with 2‐(2‐nitrovinyl)phenols has been established, thus providing a range of structurally diverse polysubstituted chromanes in good yields and excellent stereoselectivities (up t...
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| Published in | Advanced synthesis & catalysis Vol. 361; no. 19; pp. 4611 - 4622 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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08.10.2019
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| Abstract | A nickel(II)/diamine‐catalyzed diastereo‐ and enantioselective Michael/hemiacetalization cascade reaction of α‐ketoesters with 2‐(2‐nitrovinyl)phenols has been established, thus providing a range of structurally diverse polysubstituted chromanes in good yields and excellent stereoselectivities (up to 89% yield, >20:1 dr, >99% ee). Moreover, the gram‐scale experiment was performed with only 0.5 mol% of catalyst, and tricyclic furanobenzodihydropyran compound was gained by the derivatization of product, which showed the great synthetic potential of this strategy. |
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| AbstractList | A nickel(II)/diamine‐catalyzed diastereo‐ and enantioselective Michael/hemiacetalization cascade reaction of α‐ketoesters with 2‐(2‐nitrovinyl)phenols has been established, thus providing a range of structurally diverse polysubstituted chromanes in good yields and excellent stereoselectivities (up to 89% yield, >20:1 dr, >99% ee). Moreover, the gram‐scale experiment was performed with only 0.5 mol% of catalyst, and tricyclic furanobenzodihydropyran compound was gained by the derivatization of product, which showed the great synthetic potential of this strategy. A nickel(II)/diamine-catalyzed diastereo- and enantioselective Michael/hemiacetalization cascade reaction of alpha-ketoesters with 2-(2-nitrovinyl)phenols has been established, thus providing a range of structurally diverse polysubstituted chromanes in good yields and excellent stereoselectivities (up to 89% yield, >20:1 dr, >99% ee). Moreover, the gram-scale experiment was performed with only 0.5 mol% of catalyst, and tricyclic furanobenzodihydropyran compound was gained by the derivatization of product, which showed the great synthetic potential of this strategy. A nickel(II)/diamine‐catalyzed diastereo‐ and enantioselective Michael/hemiacetalization cascade reaction of α‐ketoesters with 2‐(2‐nitrovinyl)phenols has been established, thus providing a range of structurally diverse polysubstituted chromanes in good yields and excellent stereoselectivities (up to 89% yield, >20:1 dr, >99% ee). Moreover, the gram‐scale experiment was performed with only 0.5 mol% of catalyst, and tricyclic furanobenzodihydropyran compound was gained by the derivatization of product, which showed the great synthetic potential of this strategy. magnified image |
| Author | Shen, Jia‐Huan Chen, Long Yang, Wu‐Lin Deng, Wei‐Ping |
| Author_xml | – sequence: 1 givenname: Long surname: Chen fullname: Chen, Long organization: East China University of Science and Technology – sequence: 2 givenname: Wu‐Lin surname: Yang fullname: Yang, Wu‐Lin email: yangwl@ecust.edu.cn organization: East China University of Science and Technology – sequence: 3 givenname: Jia‐Huan surname: Shen fullname: Shen, Jia‐Huan organization: East China University of Science and Technology – sequence: 4 givenname: Wei‐Ping surname: Deng fullname: Deng, Wei‐Ping email: deng@ecust.edu.cn organization: East China University of Science and Technology |
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| Keywords | nickel CHROMANS COMPLEX ASYMMETRIC-SYNTHESIS 1,3-DICARBONYL COMPOUNDS STRATEGY alpha-ketoesters asymmetric catalysis CATALYST 3+2 CYCLOADDITION chromane enantioselective cascade reaction 1,2-DICARBONYL COMPOUNDS ACCESS CONJUGATE ADDITION |
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| Snippet | A nickel(II)/diamine‐catalyzed diastereo‐ and enantioselective Michael/hemiacetalization cascade reaction of α‐ketoesters with 2‐(2‐nitrovinyl)phenols has been... A nickel(II)/diamine-catalyzed diastereo- and enantioselective Michael/hemiacetalization cascade reaction of alpha-ketoesters with 2-(2-nitrovinyl)phenols has... |
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| SubjectTerms | asymmetric catalysis Cascade chemical reactions Chemistry Chemistry, Applied Chemistry, Organic chromane Enantiomers enantioselective cascade reaction Nickel Phenols Physical Sciences Science & Technology α-ketoesters |
| Title | Nickel(II)‐Catalyzed Diastereo‐ and Enantioselective Michael/ Hemiacetalization Cascade Reaction of α‐Ketoesters with 2‐(2‐Nitrovinyl)phenols |
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