Asymmetric α-Amination of 4-Substituted Pyrazolones Catalyzed by a Chiral Gd(OTf)3/N,N′-Dioxide Complex: Highly Enantioselective Synthesis of 4-Amino-5-pyrazolone Derivatives

被引：119

作者：

Yang, Zhigang ^{[1
]}

Wang, Zhen ^{[1
]}

Bai, Sha ^{[1
]}

Liu, Xiaohua ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 04期

基金：

中国国家自然科学基金;

关键词：

FRIEDEL-CRAFTS ALKYLATION; BETA-KETO-ESTERS; MICHAEL ADDITION; QUATERNARY STEREOCENTERS; CARBONYL-COMPOUNDS; ALDEHYDES; CONSTRUCTION; ACID; HYDROXYMETHYLATION; CYANOACETATES;

D O I：

10.1021/ol102804p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric alpha-amination of 4-substituted pyrazolones with azodicarboxylates was investigated for the first time, employing an N,N'-dioxide gadolinium(III) complex as the catalyst. The novel transformations exhibited high yield, and 4-amino-5-pyrazolone derivatives bearing a chiral quaternary center were obtained in excellent yields (up to 99%) and enantioselectivities (90%-97% ee) for a broad scope of 5-pyrazolones by using 1 mol A or only 0.05 mol % of catalyst.

引用

页码：596 / 599

页数：4

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