Chiral Squaramide‐Catalyzed Asymmetric Mannich Reactions for Synthesis of Fluorinated 3,3′‐Bisoxindoles

A squaramide‐catalyzed asymmetric Mannich reaction of 3‐fluorooxindoles to isatin‐derived imines for synthesis of fluorinated 3,3′‐bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3′‐bisoxindoles were obtained in excellent yields with excellent...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 360; no. 16; pp. 3164 - 3170
Main Authors Li, Bing‐Yu, Du, Da‐Ming
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 17.08.2018
Wiley Subscription Services, Inc
Subjects
Asymmetric catalysis
Bisoxindoles
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
Fluorination
Imines
Mannich addition
Organocatalysis
Physical Sciences
Science & Technology
Squaramides
Stereoselectivity
3,3-DISUBSTITUTED OXINDOLES
VINYL SULFONE
ACIDS
REACTIVITY
3-HALOOXINDOLES
Asymmetric catalysis
Organocatalysis
MEDICINAL CHEMISTRY
3-FLUOROOXINDOLES
EFFICIENT ACCESS
Mannich addition
ENANTIOSELECTIVE CONJUGATE ADDITION
CONSTRUCTION
Squaramides
Bisoxindoles
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Summary:A squaramide‐catalyzed asymmetric Mannich reaction of 3‐fluorooxindoles to isatin‐derived imines for synthesis of fluorinated 3,3′‐bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3′‐bisoxindoles were obtained in excellent yields with excellent diastereo‐ and enantioselectivities (up to 99% yield, >99:1 dr and >99% ee). What's more, this reaction can be gram‐scaled without compromising yield and stereoselectivity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800513