Organocatalytic cascade Michael/Michael reaction for the asymmetric synthesis of spirooxindoles containing five contiguous stereocenters
A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with exc...
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| Published in | Chemical communications (Cambridge, England) Vol. 52; no. 36; pp. 6162 - 6165 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
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Royal Soc Chemistry
01.01.2016
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| Abstract | A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with excellent stereoselectivities (up to >99 : 1 dr, 98% ee). Meanwhile, the practicality of this methodology was illustrated by a gram-scale synthesis, one-pot four-component reaction and synthetic transformation of the resulting adduct.
Squaramide-catalyzed cascade Michael/Michael reaction for the asymmetric synthesis of five-membered spirooxindoles containing five contiguous stereocenters is presented. |
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| AbstractList | A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with excellent stereoselectivities (up to >99: 1 dr, 98% ee). Meanwhile, the practicality of this methodology was illustrated by a gram-scale synthesis, one-pot four-component reaction and synthetic transformation of the resulting adduct. A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with excellent stereoselectivities (up to >99 : 1 dr, 98% ee). Meanwhile, the practicality of this methodology was illustrated by a gram-scale synthesis, one-pot four-component reaction and synthetic transformation of the resulting adduct.A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with excellent stereoselectivities (up to >99 : 1 dr, 98% ee). Meanwhile, the practicality of this methodology was illustrated by a gram-scale synthesis, one-pot four-component reaction and synthetic transformation of the resulting adduct. A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields (up to 93%) with excellent stereoselectivities (up to >99 : 1 dr, 98% ee). Meanwhile, the practicality of this methodology was illustrated by a gram-scale synthesis, one-pot four-component reaction and synthetic transformation of the resulting adduct. Squaramide-catalyzed cascade Michael/Michael reaction for the asymmetric synthesis of five-membered spirooxindoles containing five contiguous stereocenters is presented. |
| Author | Zhao, Bo-Liang Du, Da-Ming |
| AuthorAffiliation | Beijing Institute of Technology School of Chemical Engineering and Environment |
| AuthorAffiliation_xml | – sequence: 0 name: School of Chemical Engineering and Environment – sequence: 0 name: Beijing Institute of Technology |
| Author_xml | – sequence: 1 givenname: Bo-Liang surname: Zhao fullname: Zhao, Bo-Liang – sequence: 2 givenname: Da-Ming surname: Du fullname: Du, Da-Ming |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27075701$$D View this record in MEDLINE/PubMed |
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| Keywords | OXINDOLES DOMINO REACTIONS ACID ALPHA-ALKYLIDENE SUCCINIMIDES ENANTIOSELECTIVE CONSTRUCTION 1,3-DIPOLAR CYCLOADDITION |
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| Snippet | A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of five-membered spirooxindoles was developed. This reaction afforded... |
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| SubjectTerms | Adducts Asymmetry Cascades catalytic activity chemical compounds chemical reactions Chemistry Chemistry, Multidisciplinary Construction Michael reaction Physical Sciences Science & Technology Stereoselectivity Synthesis (chemistry) Transformations |
| Title | Organocatalytic cascade Michael/Michael reaction for the asymmetric synthesis of spirooxindoles containing five contiguous stereocenters |
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