Enantioselective Construction of Bispirooxindoles via Squaramide‐Catalysed Cascade Michael/Cyclization Reaction
A series of readily available 2‐(2‐oxoindolin‐3‐yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have been successfully applied to develop a bifunctional squaramide‐catalyzed cascade Michael/cyclization reaction strategy. Various cyclopentene‐b...
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| Published in | Advanced synthesis & catalysis Vol. 361; no. 14; pp. 3387 - 3393 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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11.07.2019
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| Abstract | A series of readily available 2‐(2‐oxoindolin‐3‐yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have been successfully applied to develop a bifunctional squaramide‐catalyzed cascade Michael/cyclization reaction strategy. Various cyclopentene‐bispirooxindoles with three continuous stereocenters, two of which are quaternary spiro‐stereocenters, were constructed in good yields with excellent stereoselectivities (up to >20:1 dr, >99% ee). |
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| AbstractList | A series of readily available 2‐(2‐oxoindolin‐3‐yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have been successfully applied to develop a bifunctional squaramide‐catalyzed cascade Michael/cyclization reaction strategy. Various cyclopentene‐bispirooxindoles with three continuous stereocenters, two of which are quaternary spiro‐stereocenters, were constructed in good yields with excellent stereoselectivities (up to >20:1 dr, >99% ee). A series of readily available 2‐(2‐oxoindolin‐3‐yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have been successfully applied to develop a bifunctional squaramide‐catalyzed cascade Michael/cyclization reaction strategy. Various cyclopentene‐bispirooxindoles with three continuous stereocenters, two of which are quaternary spiro‐stereocenters, were constructed in good yields with excellent stereoselectivities (up to >20:1 dr, >99% ee). magnified image |
| Author | Lin, Ye Zhao, Bo‐Liang Du, Da‐Ming |
| Author_xml | – sequence: 1 givenname: Bo‐Liang surname: Zhao fullname: Zhao, Bo‐Liang organization: Beijing Institute of Technology – sequence: 2 givenname: Ye surname: Lin fullname: Lin, Ye organization: Beijing Institute of Technology – sequence: 3 givenname: Da‐Ming surname: Du fullname: Du, Da‐Ming email: dudm@bit.edu.cn organization: Beijing Institute of Technology |
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| Keywords | Cascade reaction 3+2 ANNULATION Bispirooxindoles ASYMMETRIC-SYNTHESIS Michael/cyclization Squaramides Organocatalysis CYCLIZATION SPIROOXINDOLES |
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| Snippet | A series of readily available 2‐(2‐oxoindolin‐3‐yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have... A series of readily available 2-(2-oxoindolin-3-yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have... |
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| SubjectTerms | Bispirooxindoles Cascade reaction Catalysis Chemical synthesis Chemistry Chemistry, Applied Chemistry, Organic Cyclopentene Enantiomers Michael/cyclization Organocatalysis Physical Sciences Science & Technology Squaramides |
| Title | Enantioselective Construction of Bispirooxindoles via Squaramide‐Catalysed Cascade Michael/Cyclization Reaction |
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