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

页码：3539 / 3544

页数：6

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