Organocatalytic Biomimetic Decarboxylative Aldol Reaction of Fluorinated β‐Keto Acids with Unprotected Isatins

A facile asymmetric synthesis of fluorinated 3‐hydroxyoxindoles through the biomimetic decarboxylative aldol reaction of fluorinated β‐keto acids with unprotected isatins catalyzed by quinine‐derived urea catalyst has been achieved. One of the features of this work is that the easily available α, α‐...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-11, Vol.360 (21), p.4147-4152
Main Authors: Li, Yin‐Long, Wang, Xue‐Lin, Xiao, Dan, Liu, Ming‐Ying, Du, Yunfei, Deng, Jun
Format: Article
Language:English
Subjects:
Aldehydes
aldol reaction
Biomimetics
Chemical synthesis
di/monofluorinated oxindoles
Enantiomers
fluorinated β-keto acids
Fluorination
organocatalysis
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Summary:A facile asymmetric synthesis of fluorinated 3‐hydroxyoxindoles through the biomimetic decarboxylative aldol reaction of fluorinated β‐keto acids with unprotected isatins catalyzed by quinine‐derived urea catalyst has been achieved. One of the features of this work is that the easily available α, α‐difluoro/α‐monofluoro‐β‐keto acids have been first applied in the enantioselective synthesis of fluorinated compounds as the masked fluoroenolates. Furthermore, the utility of this method was demonstrated by its ability to access a series of difluorinated 3‐hydroxyoxindoles with up to 95% ee and monofluorinated 3‐hydroxyoxindoles with up to 90 : 10 d.r. and 94% ee.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800831