Chiral Phosphoric Acid Catalyzed Asymmetric Friedel-Crafts Alkylation of Indole with 3-Hydroxyisoindolin-1-one: Enantioselective Synthesis of 3-Indolyl-Substituted Isoindolin-1-ones

被引：57

作者：

Yu, Xiaolei ^{[1
]}

Lu, Aidang ^{[1
]}

Wang, Youming ^{[1
]}

Wu, Guiping ^{[1
]}

Song, Haibin ^{[1
]}

Zhou, Zhenghong ^{[1
]}

Tang, Chuchi ^{[1
]}

机构：

[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Enantioselectivity; Alkylation; Nitrogen heterocycles; Organocatalysis; HIGHLY DIASTEREOSELECTIVE SYNTHESIS; MICHAEL ADDITION; RECENT PROGRESS; FUNCTIONALIZATION; CYCLIZATIONS;

D O I：

10.1002/ejoc.201001408

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral phosphoric acids have been proven to be effective organocatalysts for the asymmetric Friedel-Crafts alkylation of indoles with 3-hydroxyisoindolin-1-ones. The corresponding products were obtained in excellent chemical yields (up to 99%) with moderate to excellent enantioselectivities (up to >99% ee after a single recrystallization). This is the first example of the catalytic asymmetric synthesis of valuable 3-substituted isoindolin-1-ones in high yields and enantioselectivities.

引用

页码：892 / 897

页数：6

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