Cu(II)-Mediated Aminooxygenation of Alkenylimines and Alkenylamidines with TEMPO

被引：21

作者：

Sanjaya, Stephen ^{[1
]}

Chua, Sze Hui ^{[1
]}

Chiba, Shunsuke ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

SYNLETT | 2012年 / 11期

关键词：

copper; TEMPO; dihydropyrroles (pyrrolines); dihydroimidazoles; INTRAMOLECULAR AMINOOXYGENATION; GRIGNARD-REAGENTS; NECTRISINE; AMIDINES; ALKENES;

D O I：

10.1055/s-0031-1291157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the synthesis of oxymethyl dihydropyrroles (pyrrolines) and dihydroimidazoles has been developed via Cu(II)-mediated intramolecular aminooxygenation of alkenylimines and alkenylamidines, respectively, with 2,2,6,6-tetramethyl-1-piperidinyloxy radical (TEMPO).

引用

页码：1657 / 1661

页数：5

共 30 条

[1] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

[2] Preparation and Utility of Trihaloethyl Imidates: Useful Reagents for the Synthesis of Amidines [J].

Caron, Stephane ;

Wei, Lulin ;

Douville, Jasmin ;

Ghosh, Arun .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :945-947

[3] Evolution of copper(II) as a new alkene amination promoter and catalyst [J].

Chemler, Sherry R. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) :150-158

[4] Current strategies for diversity-oriented synthesis [J].

Dandapani, Sivaraman ;

Marcaurelle, Lisa A. .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (03) :362-370

[5]

Eicher T., 2003, the Chemistry of Heterocycles, V2nd

[6] Copper Catalyzed Enantioselective Intramolecular Aminooxygenation of Alkenes [J].

Fuller, Peter H. ;

Kim, Jin-Woo ;

Chemler, Sherry R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (52) :17638-+

[7]

Gribble G. W., 2008, PROGR HETEROCYCLIC C, V20

[8] Stereoselective synthesis of the α-glucosidase inhibitor nectrisine [J].

Hulme, AN ;

Montgomery, CH .

TETRAHEDRON LETTERS, 2003, 44 (41) :7649-7653

[9]

Joule J.A., 2010, Heterocyclic Chemistry, V5th

[10]

Katritzky A. R., 1996, COMPREHENSIVE HETERO, VII

← 1 2 3 →