Asymmetric Organocatalytic Conjugate Addition of Electron‐Rich Phenols and 1,3‐Dicarbonyls to Arylsulfonyl Indoles in an Oil‐Water Biphasic System

The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts has been established. The chiral 3,3‐disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselecti...

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Published inEuropean journal of organic chemistry Vol. 2019; no. 33; pp. 5815 - 5823
Main Authors Han, Jeng‐Liang, Liao, Yu‐Ting, Chang, Chia‐Hao
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.09.2019
Wiley Subscription Services, Inc
Subjects
Asymmetry
Biphasic catalysis
Chemistry
Chemistry, Organic
Conjugates
Indoles
Organocatalysis
Phenols
Physical Sciences
Science & Technology
Stereoselectivity
Synthetic methods
3,3-DISUBSTITUTED OXINDOLES
1,6-CONJUGATE ADDITION
GENERATED IN-SITU
ORTHO-QUINONE METHIDES
BETA-SUBSTITUTED TRYPTOPHANS
ENANTIOSELECTIVE MICHAEL ADDITION
Organocatalysis
NONCOVALENT ORGANOCATALYSIS
FLEXIBLE GATEWAY
ALPHA-AMIDO SULFONES
Phenols
Biphasic catalysis
Synthetic methods
Indoles
FRIEDEL-CRAFTS REACTION
Online AccessGet full text
ISSN1434-193X
1099-0690
DOI10.1002/ejoc.201900962

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Abstract The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts has been established. The chiral 3,3‐disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselectivies (up to 98 % ee). This study showed that the oil‐water biphasic system contributed to the high efficiency and stereoselectivity. The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts have been established. The chiral 3,3‐disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselectivies (up to 98 % ee). This study showed that oil‐water biphasic system contributed to the high efficiency and stereoselectivity.
AbstractList The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts has been established. The chiral 3,3‐disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselectivies (up to 98 % ee ). This study showed that the oil‐water biphasic system contributed to the high efficiency and stereoselectivity.
The asymmetric conjugate addition of electron-rich phenols and 1,3-dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts has been established. The chiral 3,3-disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselectivies (up to 98 % ee). This study showed that the oil-water biphasic system contributed to the high efficiency and stereoselectivity.
The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts has been established. The chiral 3,3‐disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselectivies (up to 98 % ee). This study showed that the oil‐water biphasic system contributed to the high efficiency and stereoselectivity. The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts have been established. The chiral 3,3‐disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselectivies (up to 98 % ee). This study showed that oil‐water biphasic system contributed to the high efficiency and stereoselectivity.
Author Han, Jeng‐Liang
Liao, Yu‐Ting
Chang, Chia‐Hao
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  organization: Chung Yuan Christian University
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Keywords 3,3-DISUBSTITUTED OXINDOLES
1,6-CONJUGATE ADDITION
GENERATED IN-SITU
ORTHO-QUINONE METHIDES
BETA-SUBSTITUTED TRYPTOPHANS
ENANTIOSELECTIVE MICHAEL ADDITION
Organocatalysis
NONCOVALENT ORGANOCATALYSIS
FLEXIBLE GATEWAY
ALPHA-AMIDO SULFONES
Phenols
Biphasic catalysis
Synthetic methods
Indoles
FRIEDEL-CRAFTS REACTION
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  doi: 10.1002/chem.201204522
SSID ssj0009661
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Snippet The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts has been...
The asymmetric conjugate addition of electron-rich phenols and 1,3-dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts has been...
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SubjectTerms Asymmetry
Biphasic catalysis
Chemistry
Chemistry, Organic
Conjugates
Indoles
Organocatalysis
Phenols
Physical Sciences
Science & Technology
Stereoselectivity
Synthetic methods
Title Asymmetric Organocatalytic Conjugate Addition of Electron‐Rich Phenols and 1,3‐Dicarbonyls to Arylsulfonyl Indoles in an Oil‐Water Biphasic System
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.201900962
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