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

[11] Meldrum's Acids and 5-Alkylidene Meldrum's Acids in Catalytic Carbon-Carbon Bond-Forming Processes [J].

Dumas, Aaron M. ;

Fillion, Eric .

ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (03) :440-454

[12] THIOALKYLATION OF MELDRUMS ACID - PROTECTED ALKYLIDENE DERIVATIVES OF ISOPROPYLIDENE MALONATE [J].

EBERLE, M ;

LAWTON, RG .

HELVETICA CHIMICA ACTA, 1988, 71 (08) :1974-1982

[13] Organocatalytic Asymmetric Aza-Michael Additions [J].

Enders, Dieter ;

Wang, Chuan ;

Liebich, Jens X. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (42) :11058-11076

[14] Organocatalytic Enantioselective Synthesis of Pyrazolidines, Pyrazolines and Pyrazolidinones [J].

Fernandez, Maitane ;

Reyes, Efraim ;

Vicario, Jose L. ;

Badia, Dolores ;

Carrillo, Luisa .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) :371-376

[15] Meldrum's acid in multicomponent reactions:: Applications to combinatorial and diversity-oriented synthesis [J].

Gerencsér, J ;

Dormán, G ;

Darvas, F .

QSAR & COMBINATORIAL SCIENCE, 2006, 25 (5-6) :439-448

[16] Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions [J].

Gould, Eoin ;

Lebl, Tomas ;

Slawin, Alexandra M. Z. ;

Reid, Mark ;

Smith, Andrew D. .

TETRAHEDRON, 2010, 66 (46) :8992-9008

[17]

Hashimoto T., 2009, HDB CYCLIZATION REAC, P87

[18] Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines: An Umpolung Strategy [J].

Hashimoto, Takuya ;

Omote, Masato ;

Maruoka, Keiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (15) :3489-3492

[19] A Catalytic Asymmetric Ugi-type Reaction With Acyclic Azomethine Imines [J].

Hashimoto, Takuya ;

Kimura, Hidenori ;

Kawamata, Yu ;

Maruoka, Keiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) :7279-7281

[20]

Hashimoto T, 2011, NAT CHEM, V3, P642, DOI [10.1038/NCHEM.1096, 10.1038/nchem.1096]

← 1 2 3 4 5 6 →