Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: Improved reaction conditions and expanded substrate scope

被引：101

作者：

Zabawa, Thomas P. ^{[1
]}

Chemler, Sherry R. ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 10期

关键词：

D O I：

10.1021/ol0706713

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper(II) carboxylate promoted diamination reaction has been improved by the use of the organic soluble copper(II) neodecanoate [Cu( ND)(2)]. Cu(ND)(2) allowed the less-polar solvent dichloroethane (DCE) to be used, and as a consequence, decomposition of less-reactive substrates could be avoided. High diastereoselectivity was observed in the synthesis of 2,5-disubstituted pyrrolidines. Ureas, bis(anilines), and alpha-amido pyrroles derived from 2-allylaniline could also participate in the diamination reaction.

引用

页码：2035 / 2038

页数：4

共 28 条

[1] ANDREWS P, 1998, MED REV REV, V3, P147
[2] Potent and selective bicyclic lactam inhibitors of thrombin. Part 4: Transition state inhibitors
Bachand, B
Tarazi, M
St-Denis, Y
Edmunds, JJ
Winocour, PD
Leblond, L
Siddiqui, MA
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (03) : 287 - 290
[3] Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes
Bar, GLJ
Lloyd-Jones, GC
Booker-Milburn, KI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) : 7308 - 7309
[4] Discovery and optimization of 2-aryl oxazolo-pyrimidines as adenosine kinase inhibitors using liquid phase parallel synthesis
Bauser, M
Delapierre, G
Hauswald, M
Flessner, T
D'Urso, D
Hermann, A
Beyreuther, B
De Vry, J
Spreyer, P
Reissmüller, E
Meier, H
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (08) : 1997 - 2000
[5] MIANSERIN - REVIEW OF ITS PHARMACOLOGICAL PROPERTIES AND THERAPEUTIC EFFICACY IN DEPRESSIVE-ILLNESS
BROGDEN, RN
HEEL, RC
SPEIGHT, TM
AVERY, GS
[J]. DRUGS, 1978, 16 (04) : 273 - 301
[6] Designing non-peptide peptidomimetics in the 21st century: Inhibitors targeting conformational ensembles
Bursavich, MG
Rich, DH
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) : 541 - 558
[7] Copper(II) complexes of inverted porphyrin and its methylated derivatives
Chmielewski, PJ
Latos-Grazynski, L
Schmidt, I
[J]. INORGANIC CHEMISTRY, 2000, 39 (24) : 5475 - 5482
[8] A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes
Du, Haifeng
Zhao, Baoguo
Shi, Yian
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (04) : 762 - 763
[9] Epidemiology, burden and control of schistosomiasis with particular consideration to past and current treatment trends
Fenwick, Alan
Keiser, Jennifer
Utzinger, Jurg
[J]. DRUGS OF THE FUTURE, 2006, 31 (05) : 413 - 425
[10] HYDROXYL RADICAL INDUCED DECARBOXYLATION AND DEAMINATION OF 2-METHYLALANINE CATALYZED BY COPPER IONS
GOLDSTEIN, S
CZAPSKI, G
COHEN, H
MEYERSTEIN, D
[J]. INORGANIC CHEMISTRY, 1992, 31 (12) : 2439 - 2444

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