Chiral Brønsted acid-catalyzed enantioselective friedel-crafts reaction of 4,7-dihydroindoles with trifluoromethyl ketones

Teng Wang; Guang Wu Zhang; Yuou Teng; Jing Nie; Yan Zheng; Jun An Ma

doi:10.1002/adsc.201000510

Chiral Brønsted acid-catalyzed enantioselective friedel-crafts reaction of 4,7-dihydroindoles with trifluoromethyl ketones

Teng Wang
, Guang Wu Zhang
, Yuou Teng
, Jing Nie
, Yan Zheng
, Jun An Ma^*

^*此作品的通讯作者

Tianjin University
Nankai University

科研成果: 期刊稿件 › 文章 › 同行评审

48 引用（Scopus）

摘要

In the presence of chiral phosphoric acid, an enantioselective Friedel-Crafts reaction of 4,7-dihydroindoles with aromatic trifluoromethyl ketones and ethyl 4,4,4-trifluoroacetoacetate has been realized. A series of 2-substituted 4,7-dihydroindoles with a trifluoromethylated tertiary alcohol moiety were obtained in 45-95% yields with 60-93% ee. Furthermore, 2-functionalized indole derivatives could be produced through a one-pot process.

源语言	英语
页（从-至）	2773-2777
页数	5
期刊	Advanced Synthesis and Catalysis
卷	352
期	16
DOI	https://doi.org/10.1002/adsc.201000510
出版状态	已出版 - 2 11月 2010
已对外发布	是

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@article{076bb226e2f94044a6f3d78e3b83c9ed,

title = "Chiral Br{\o}nsted acid-catalyzed enantioselective friedel-crafts reaction of 4,7-dihydroindoles with trifluoromethyl ketones",

abstract = "In the presence of chiral phosphoric acid, an enantioselective Friedel-Crafts reaction of 4,7-dihydroindoles with aromatic trifluoromethyl ketones and ethyl 4,4,4-trifluoroacetoacetate has been realized. A series of 2-substituted 4,7-dihydroindoles with a trifluoromethylated tertiary alcohol moiety were obtained in 45-95\% yields with 60-93\% ee. Furthermore, 2-functionalized indole derivatives could be produced through a one-pot process.",

keywords = "4,7-dihydroindoles, Br{\o}nsted acids, Friedel-Crafts reaction, enantioselectivity, trifluoromethyl-substituted compounds",

author = "Teng Wang and Zhang, \{Guang Wu\} and Yuou Teng and Jing Nie and Yan Zheng and Ma, \{Jun An\}",

year = "2010",

month = nov,

day = "2",

doi = "10.1002/adsc.201000510",

language = "英语",

volume = "352",

pages = "2773--2777",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "16",

}

TY - JOUR

T1 - Chiral Brønsted acid-catalyzed enantioselective friedel-crafts reaction of 4,7-dihydroindoles with trifluoromethyl ketones

AU - Wang, Teng

AU - Zhang, Guang Wu

AU - Teng, Yuou

AU - Nie, Jing

AU - Zheng, Yan

AU - Ma, Jun An

PY - 2010/11/2

Y1 - 2010/11/2

N2 - In the presence of chiral phosphoric acid, an enantioselective Friedel-Crafts reaction of 4,7-dihydroindoles with aromatic trifluoromethyl ketones and ethyl 4,4,4-trifluoroacetoacetate has been realized. A series of 2-substituted 4,7-dihydroindoles with a trifluoromethylated tertiary alcohol moiety were obtained in 45-95% yields with 60-93% ee. Furthermore, 2-functionalized indole derivatives could be produced through a one-pot process.

AB - In the presence of chiral phosphoric acid, an enantioselective Friedel-Crafts reaction of 4,7-dihydroindoles with aromatic trifluoromethyl ketones and ethyl 4,4,4-trifluoroacetoacetate has been realized. A series of 2-substituted 4,7-dihydroindoles with a trifluoromethylated tertiary alcohol moiety were obtained in 45-95% yields with 60-93% ee. Furthermore, 2-functionalized indole derivatives could be produced through a one-pot process.

KW - 4,7-dihydroindoles

KW - Brønsted acids

KW - Friedel-Crafts reaction

KW - enantioselectivity

KW - trifluoromethyl-substituted compounds

UR - https://www.scopus.com/pages/publications/78349262741

U2 - 10.1002/adsc.201000510

DO - 10.1002/adsc.201000510

M3 - 文章

AN - SCOPUS:78349262741

SN - 1615-4150

VL - 352

SP - 2773

EP - 2777

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 16

ER -

Chiral Brønsted acid-catalyzed enantioselective friedel-crafts reaction of 4,7-dihydroindoles with trifluoromethyl ketones

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