Organocatalysed multicomponent synthesis of pyrazolidinones: Meldrum's acid approach

被引：36

作者：

Pair, Etienne ^{[1
,2
]}

Berini, Christophe ^{[1
,2
]}

Noel, Romain ^{[1
,2
]}

Sanselme, Morgane ^{[3
]}

Levacher, Vincent ^{[1
,2
]}

Briere, Jean-Francois ^{[1
,2
]}

机构：

[1] Univ Rouen, CNRS, INSA Rouen, IRCOF,FR 3038, F-76821 Mont St Aignan, France

[2] Normandie Univ, COBRA, UMR 6014, F-76821 Mont St Aignan, France

[3] Normandie Universite Univ, Lab SMS EA3233 IMR 4114, Rouen, France

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 71期

关键词：

ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; AZOMETHINE IMINES; NATURAL-PRODUCTS; MICHAEL; DIVERSITY; ALDER;

D O I：

10.1039/c4cc04852k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We discovered a novel organocatalysed multicomponent domino Knoevenagel-aza-Michael-cyclocondensation reaction leading to an unprecedented straightforward synthesis of 1,5-diazabicyclo[3.3.0]octane-2,6-diones. The specific capability of the (DHQ)(2)PHAL organocatalyst in this process was also highlighted to eventually furnish the corresponding bicyclopyrazolidinones with up to 96:4 er.

引用

页码：10218 / 10221

页数：4

共 53 条

[1] Asymmetric organocascades involving the formation of two C-heteroatom bonds from two distinct heteroatoms [J].

Bonne, Damien ;

Constantieux, Thierry ;

Coquerel, Yoann ;

Rodriguez, Jean .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (20) :3969-3973

[2] The α-effect in cyclic secondary amines: new scaffolds for iminium ion accelerated transformations [J].

Brazier, John B. ;

Cavill, Julie L. ;

Elliott, Richard L. ;

Evans, Gareth ;

Gibbs, Timothy J. K. ;

Jones, Ian L. ;

Platts, James A. ;

Tomkinson, Nicholas C. O. .

TETRAHEDRON, 2009, 65 (48) :9961-9966

[3] Direct amination of homoenolates catalyzed by N-Heterocyclic carbenes [J].

Chan, Audrey ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2740-+

[4] Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding [J].

Chen, Wei ;

Du, Wei ;

Duan, Yong-Zheng ;

Wu, Yong ;

Yang, Sheng-Yong ;

Chen, Ying-Chun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7667-7670

[5] Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes [J].

Chen, Wei ;

Yuan, Xiang-Hong ;

Li, Rui ;

Du, Wei ;

Wu, Yong ;

Ding, Li-Sheng ;

Chen, Ying-Chun .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1818-1822

[6] MONOALKYLIDENES OF MELDRUMS ACID [J].

CHHABRA, BR ;

BOLTE, ML ;

CROW, WD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (08) :1795-1797

[7] Recent developments in asymmetric multicomponent reactions [J].

de Graaff, Corien ;

Ruijter, Eelco ;

Orru, Romano V. A. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3969-4009

[8] SYNTHESES BY MEANS OF 1-ALKYLIDENE- AND 1-(ARYLALKYLIDENE)-3-PYRAZOLIDONE N,N-BETAINES A NEW TYPE OF STABLE AZOMETHINE IMINE [J].

DORN, H ;

OTTO, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (03) :214-&

[9] REACTION OF PYRAZOLID-3-ONE WITH CARBONYL COMPOUNDS [J].

DORN, H ;

OTTO, A .

CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (09) :3287-&

[10] A general and practical preparation of alkylidene Meldrum's acids [J].

Dumas, Aaron M. ;

Seed, Adam ;

Zorzitto, Alexander K. ;

Fillion, Eric .

TETRAHEDRON LETTERS, 2007, 48 (40) :7072-7074

← 1 2 3 4 5 6 →