A Cooperative Participation of the Amido Group in the Organocatalytic Construction of All-Carbon Quaternary Stereocenters by Michael Addition with β-Ketoamides

被引：41

作者：

Duque, Maria del Mar Sanchez ^{[1
]}

Basle, Olivier ^{[1
]}

Isambert, Nicolas ^{[1
]}

Gaudel-Siri, Anouk ^{[1
]}

Genisson, Yves ^{[2
]}

Plaquevent, Jean-Christophe ^{[2
]}

Rodriguez, Jean ^{[1
]}

Constantieux, Thierry ^{[1
]}

机构：

[1] Aix Marseille Univ, ISm2, UMR CNRS 6263, Ctr St Jerome,Serv 531, F-13397 Marseille 20, France

[2] Univ Toulouse 3, LSPCMIB, UMR CNRS 5068, F-31062 Toulouse 9, France

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 13期

关键词：

ASYMMETRIC CONJUGATE ADDITION; SITE-ISOLATED BASE; 1,3-DICARBONYL COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; KETOESTERS; CASCADES; DERIVATIVES; CYCLIZATION; CATALYSIS; THIOUREA;

D O I：

10.1021/ol200924e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The secondary amido group of a-substituted beta-ketoamides plays a crucial role in the control of the reactivity and spatial arrangement (selectivity) in the organocatalyzed Michael addition to unsaturated carbonyls. This results in an unprecedented activation mode of substrates through H-bonding interactions allowing the construction of enantiomerically enriched functionalized all-carbon quaternary centers and spiroaminals of high synthetic potential.

引用

页码：3296 / 3299

页数：4

共 61 条

[1]

ADAM AW, 2007, ANGEW CHEM INT EDIT, V46, P5428

[2] Enantioselective Robinson-Type Annulation Reaction Catalyzed by Chiral Phosphoric Acids [J].

Akiyama, Takahiko ;

Katoh, Takuya ;

Mori, Keiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4226-4228

[3] Formation of all-carbon quaternary centers by copper-catalyzed asymmetric conjugate addition [J].

Alexakis, Alexandre ;

Vuagnoux-d'Augustin, Magali ;

Martin, David ;

Kehrli, Stefan ;

Palais, Laetitia ;

Henon, Hne ;

Hawner, Christine .

CHIMIA, 2008, 62 (06) :461-464

[4] A novel organocatalytic tool for the iminium activation of α,β-unsaturated ketones [J].

Bartoli, Giuseppe ;

Melchiorre, Paolo .

SYNLETT, 2008, (12) :1759-1772

[5] Highly Diastereo- and Enantioselective Organocatalytic Michael Addition of α-Ketoamides to Nitroalkenes [J].

Basle, Olivier ;

Raimondi, Wilfried ;

Sanchez Duque, Maria del Mar ;

Bonne, Damien ;

Constantieux, Thierry ;

Rodriguez, Jean .

ORGANIC LETTERS, 2010, 12 (22) :5246-5249

[6] Organocatalytic Formation of Quaternary Stereocenters [J].

Bella, Marco ;

Gasperi, Tecla .

SYNTHESIS-STUTTGART, 2009, (10) :1583-1614

[7] Organocatalysis-after the gold rush [J].

Bertelsen, Soren ;

Jorgensen, Karl Anker .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189

[8] Organocatalytic Activity of N-Heterocyclic Carbenes in the Michael Addition of 1,3-Dicarbonyl Compounds: Application to a Stereoselective Spirocyclization Sequence [J].

Boddaert, Thomas ;

Coquerel, Yoann ;

Rodriguez, Jean .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) :1744-1748

[9] Sequential Organocatalyzed Michael Addition/[3+2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids [J].

Bonne, Damien ;

Salat, Lydie ;

Dulcere, Jean-Pierre ;

Rodriguez, Jean .

ORGANIC LETTERS, 2008, 10 (23) :5409-5412

[10] Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of β-ketoesters [J].

Capuzzi, Marinella ;

Perdicchia, Dario ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (01) :128-135

← 1 2 3 4 5 6 7 →