Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β-Nitrostyrenes Catalyzed by Bifunctional Thioureas: A Simple Access to 2-Functionalized Indoles

被引：31

作者：

Liu, Yao-Zong ^{[1
]}

Cheng, Rui-Ling ^{[1
]}

Xu, Peng-Fei ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 08期

关键词：

FRIEDEL-CRAFTS ALKYLATIONS; HIGHLY ENANTIOSELECTIVE FRIEDEL; CONJUGATE ADDITION; 4,7-DIHYDROINDOLES; NITROOLEFINS; GLYOXYLATE; ENONES; REARRANGEMENT; NITROALKENES; AMINES;

D O I：

10.1021/jo102022g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric Michael addition of 1-acetylindolin-3-ones to beta-nitrostyrenes has been developed. 2-Substituted indolin-3-one derivatives were obtained with excellent yields (up to 99%) and good stereoselectivities (up to 28:1 dr and 92% ee), which could be transformed into 2-functionalized indoles easily without racemization. This achievement might further contribute to the chemistry and pharmacology of indole-related compounds.

引用

页码：2884 / 2887

页数：4

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