Enantioselective Rhodium-Catalyzed [4+2] Cycloaddition of α,β-Unsaturated Imines and Isocyanates

被引：41

作者：

Oberg, Kevin M. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 13期

关键词：

DIELS-ALDER REACTIONS; ALKENYL ISOCYANATES; ASYMMETRIC-SYNTHESIS; TERMINAL ALKYNES; 1-AZADIENES; INSERTION; NICKEL(0);

D O I：

10.1021/ja200766k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A [4 + 2] cycloaddition of alpha,beta-unsaturated imines and isocyanates catalyzed by a phosphoramidite rhodium complex provides pyrimidinones in good yields and high enantioselectivities.

引用

页码：4785 / 4787

页数：3

共 39 条

[11] 1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles [J].

Groenendaal, Bas ;

Ruijter, Eelco ;

Orru, Romano V. A. .

CHEMICAL COMMUNICATIONS, 2008, (43) :5474-5489

[12] Asymmetric Organocatalytic Tandem Reaction to Chiral Pyrimidinone Derivatives using Urea as Dinitrogen Source [J].

He, Zhao-Quan ;

Zhou, Quan ;

Wu, Li ;

Chen, Ying-Chun .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (11-12) :1904-1908

[13] DIAZANICKELACYCLOPENTANONES SYNTHESIZED FROM NICKEL(0), IMINES AND ISOCYANATES [J].

HOBERG, H ;

SUMMERMANN, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 253 (03) :383-389

[14] Highly enantioseletive biginelli reaction using a new chiral ytterbium catalyst: Asymmetric synthesis of dihydropyrimidines [J].

Huang, YJ ;

Yang, FY ;

Zhu, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16386-16387

[15] Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C-H/N-H Activation [J].

Hyster, Todd K. ;

Rovis, Tomislav .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) :10565-10569

[16] Recent advances in synthetic applications of azadienes [J].

Jayakumar, S ;

Ishar, MPS ;

Mahajan, MP .

TETRAHEDRON, 2002, 58 (03) :379-471

[17] Enantioselective [4+2] cycloaddition of ketenes and 1-azadienes catalyzed by N-heterocyclic carbenes [J].

Jian, Teng-Yue ;

Shao, Pan-Lin ;

Ye, Song .

CHEMICAL COMMUNICATIONS, 2011, 47 (08) :2381-2383

[18] Biologically active dihydropyrimidones of the Biginelli-type - a literature survey [J].

Kappe, CO .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (12) :1043-1052

[19] Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog [J].

Kappe, CO .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (12) :879-888

[20] A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-acyliminium ion intermediate [J].

Kappe, CO .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7201-7204

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