Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One‐pot Three‐component Sequential Cascade Reactions

A bifunctional squaramide‐catalyzed one‐pot three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamo...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 361; no. 14; pp. 3412 - 3419
Main Authors Zhao, Bo‐Liang, Du, Da‐Ming
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 11.07.2019
Wiley Subscription Services, Inc
Subjects
Cascade chemical reactions
Cascade reaction
Chemical reactions
Chemistry
Chemistry, Applied
Chemistry, Organic
Enantiomers
Michael/cyclization
Michael/Mannich
Organocatalysis
Physical Sciences
Science & Technology
Spirooxindoles
Cascade reaction
Spirooxindoles
DOMINO REACTIONS
Michael/cyclization
1,3-DIPOLAR CYCLOADDITION
CONSTRUCTION
Organocatalysis
Michael/Mannich
N-2,2,2-TRIFLUOROETHYLISATIN KETIMINES
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Summary:A bifunctional squaramide‐catalyzed one‐pot three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamoyl‐3‐ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction of bispirooxindole‐spirooxindoles with seven stereocenters, of which three are quaternary spiro‐stereocenters.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 14
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900218