Facile creation of 3-indolyl-3-hydroxy-2-oxindoles by an organocatalytic enantioselective friedel-crafts reaction of indoles with isatins

Jing Deng; Shilei Zhang; Peng Ding; Hualiang Jiang; Wei Wang; Jian Li

doi:10.1002/adsc.200900851

Facile creation of 3-indolyl-3-hydroxy-2-oxindoles by an organocatalytic enantioselective friedel-crafts reaction of indoles with isatins

Jing Deng
, Shilei Zhang
, Peng Ding
, Hualiang Jiang
, Wei Wang
, Jian Li

Research output: Contribution to journal › Article › peer-review

102 Scopus citations

Abstract

The first direct enantioselective FriedelCrafts reaction of indoles with isatins has been developed. The process is catalyzed by simple cupreine under mild reaction conditions and affords synthetically and biologically interesting, chiral 3-indolyl-3-hydroxy-2-oxindoles in good yields (6897%) and with high enantioselectivities (76-91%).

Original language	English (US)
Pages (from-to)	833-838
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	352
Issue number	5
DOIs	https://doi.org/10.1002/adsc.200900851
State	Published - Mar 22 2010
Externally published	Yes

Keywords

Asymmetric friedel-crafts reaction
Indoles
Isatins
Organocatalysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200900851

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title = "Facile creation of 3-indolyl-3-hydroxy-2-oxindoles by an organocatalytic enantioselective friedel-crafts reaction of indoles with isatins",

abstract = "The first direct enantioselective FriedelCrafts reaction of indoles with isatins has been developed. The process is catalyzed by simple cupreine under mild reaction conditions and affords synthetically and biologically interesting, chiral 3-indolyl-3-hydroxy-2-oxindoles in good yields (6897\%) and with high enantioselectivities (76-91\%).",

keywords = "Asymmetric friedel-crafts reaction, Indoles, Isatins, Organocatalysis",

author = "Jing Deng and Shilei Zhang and Peng Ding and Hualiang Jiang and Wei Wang and Jian Li",

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T1 - Facile creation of 3-indolyl-3-hydroxy-2-oxindoles by an organocatalytic enantioselective friedel-crafts reaction of indoles with isatins

AU - Deng, Jing

AU - Zhang, Shilei

AU - Ding, Peng

AU - Jiang, Hualiang

AU - Wang, Wei

AU - Li, Jian

PY - 2010/3/22

Y1 - 2010/3/22

N2 - The first direct enantioselective FriedelCrafts reaction of indoles with isatins has been developed. The process is catalyzed by simple cupreine under mild reaction conditions and affords synthetically and biologically interesting, chiral 3-indolyl-3-hydroxy-2-oxindoles in good yields (6897%) and with high enantioselectivities (76-91%).

AB - The first direct enantioselective FriedelCrafts reaction of indoles with isatins has been developed. The process is catalyzed by simple cupreine under mild reaction conditions and affords synthetically and biologically interesting, chiral 3-indolyl-3-hydroxy-2-oxindoles in good yields (6897%) and with high enantioselectivities (76-91%).

KW - Asymmetric friedel-crafts reaction

KW - Indoles

KW - Isatins

KW - Organocatalysis

UR - https://www.scopus.com/pages/publications/77950360054

UR - https://www.scopus.com/pages/publications/77950360054#tab=citedBy

U2 - 10.1002/adsc.200900851

DO - 10.1002/adsc.200900851

M3 - Article

AN - SCOPUS:77950360054

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VL - 352

SP - 833

EP - 838

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 5

ER -

Facile creation of 3-indolyl-3-hydroxy-2-oxindoles by an organocatalytic enantioselective friedel-crafts reaction of indoles with isatins

Abstract

Keywords

ASJC Scopus subject areas

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