Organocatalytic Enantioselective aza‐Friedel‐Crafts Reactions of Pyrazolinone Ketimines with Hydroxyindoles and Electron‐Rich Phenols

A variety of enantioenriched indole derivatives substituted in the benzene ring were synthesised via an organocatalytic asymmetric aza‐Friedel‐Crafts reaction of pyrazolinone ketimines with hydroxyindoles. This reaction was also applicabled to electron‐rich phenols, yielding the desired products in...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 360; no. 10; pp. 2049 - 2054
Main Authors Yang, Zhong‐Tao, Yang, Wu‐Lin, Chen, Long, Sun, Hao, Deng, Wei‐Ping
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 16.05.2018
Wiley Subscription Services, Inc
Subjects
asymmetric organo-catalysis
aza-Friedel-Crafts
Benzene
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
Derivatives
electron-rich phenols
Friedel-Crafts reaction
hydroxyindoles
Imines
Phenols
Physical Sciences
pyrazolinone ketimines
Science & Technology
PALLADIUM
electron-rich phenols
ASYMMETRIC-SYNTHESIS
ALKYLATION
PYRAZOLONES
ARYLATION
asymmetric organo-catalysis
pyrazolinone ketimines
QUATERNARY
hydroxyindoles
INDOLES
FUNCTIONALIZATION
aza-Friedel-Crafts
STEREOCONTROLLED CONSTRUCTION
DERIVATIVES
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Summary:A variety of enantioenriched indole derivatives substituted in the benzene ring were synthesised via an organocatalytic asymmetric aza‐Friedel‐Crafts reaction of pyrazolinone ketimines with hydroxyindoles. This reaction was also applicabled to electron‐rich phenols, yielding the desired products in high yields (up to 99%) and excellent stereo‐selectivities (91–99% ee). Moreover, this method presents its potential in the synthesis of structurally novel indole‐pyrazolinone conjugate derivatives.
Bibliography:ObjectType-Article-1
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800181