Copper-Catalyzed Enantioselective Inverse Electron-Demand Hetero-Diels-Alder Reactions of Diazadienes with Enol Ethers: Efficient Synthesis of Chiral Pyridazines

被引：91
作者：
Gao, Shuang [1 ,2 ]
Chen, Jia-Rong [1 ,2 ,3 ]
Hu, Xiao-Qiang [1 ,2 ]
Cheng, Hong-Gang [1 ,2 ]
Lu, Liang-Qiu [1 ,2 ]
Xiao, Wen-Jing [1 ,2 ]
机构：
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China
[2] Collaborat Ctr Chem Sci & Engn Tianjin, Tianjin, Peoples R China
[3] Wuhan Inst Technol, Key Lab Green Chem Proc, Minist Educ, Wuhan 430079, Hubei, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 18期
基金：
美国国家科学基金会;
关键词：
chiral lewis acid catalysis; 1; 2-diaza-1; 3-dienes; inverse electron-demand hetero-Diels-Alder (IEDDA) reaction; pyridazine derivatives; ACID CATALYSIS; IMINES; CYCLOADDITION; HYDRAZONES; ACCESS; AZOALKENES; ALDEHYDES; STRATEGY; OLEFINS;
D O I：
10.1002/adsc.201300723
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly efficient and enantioselective inverse electron-demand hetero-Diels-Alder reaction of in situ generated 1,2-diaza-1,3-dienes with enol ethers has been developed with the use of a chiral copper/bisoxazoline complex as the catalyst. The reaction exhibits high enantioselectivity (up to 90% ee) and provides a robust and powerful method to synthesize a variety of structurally diverse and densely substituted chiral pyridazine derivatives in good to excellent yields.
引用
收藏
页码：3539 / 3544
页数：6
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