Enantioselective Synthesis of Dihydropyrazoles by Formal [4+1] Cycloaddition of in Situ-Derived Azoalkenes and Sulfur Ylides

被引：216

作者：

Chen, Jia-Rong ^{[1
,2
]}

Dong, Wan-Rong ^{[1
]}

Candy, Mathieu ^{[1
]}

Pan, Fang-Fang ^{[3
]}

Joerres, Manuel ^{[1
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

[2] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

[3] Rhein Westfal TH Aachen, Inst Inorgan Chem, D-52074 Aachen, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 16期

基金：

中国国家自然科学基金;

关键词：

ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; CATALYTIC ASYMMETRIC-SYNTHESIS; AZOMETHINE IMINES; 1,3-DIPOLAR CYCLOADDITIONS; TERMINAL ALKYNES; NITRILE IMINES; DERIVATIVES; ALDEHYDES; KETONES; CYCLOPROPANATION;

D O I：

10.1021/ja301196x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented strategy to access highly enantioenriched dihydropyrazoles is described. It involves formal [4+1] cycloadditions of in situ-derived azoalkenes and sulfur ylides catalyzed by a chiral copper/Tol-BINAP complex. A variety of synthetically and biologically important dihydropyrazoles have been obtained with high enantioselectivities (up to 97:3 er) in good yields (83-97%).

引用

页码：6924 / 6927

页数：4

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