Catalytic Batch and Continuous Flow Production of Highly Enantioenriched Cyclohexane Derivatives with Polymer-Supported Diarylprolinol Silyl Ethers

被引:72
作者
Alza, Esther [1 ]
Sayalero, Sonia [1 ]
Cambeiro, Xacobe C. [1 ]
Martin-Rapun, Rafael [1 ]
Miranda, Pedro O. [1 ]
Pericas, Miquel A. [1 ,2 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
关键词
asymmetric organocatalysis; domino process; Michael addition; Knoevenagel condensation; flow reactors; TRICYCLIC CARBON FRAMEWORKS; ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; MICHAEL ADDITION; DOMINO REACTIONS; CASCADE; IMMOBILIZATION;
D O I
10.1055/s-0030-1259528
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diarylprolinol silyl ethers immobilized onto polystyrene have been employed as catalysts in the enantioselective domino Michael-Knoevenagel reaction of dimethyl 3-oxoglutarate and 3-substituted acrolein derivatives, including aliphatic ones. The best catalyst allows the preparation of highly functionalized cyclohexane derivatives in a straightforward and efficient manner, both under batch and continuous flow conditions.
引用
收藏
页码:464 / 468
页数:5
相关论文
共 62 条
[1]   Highly enantioselective Michael additions in water catalyzed by a PS-Supported pyrrolidine [J].
Alza, Esther ;
Cambeiro, Xacobe C. ;
Jimeno, Ciril ;
Pericas, Miquel A. .
ORGANIC LETTERS, 2007, 9 (19) :3717-3720
[2]   A Highly Selective, Polymer-Supported Organocatalyst for Michael Additions with Enzyme-Like Behavior [J].
Alza, Esther ;
Pericas, Miquel A. .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) :3051-3056
[3]   A Solid-Supported Organocatalyst for Highly Stereoselective, Batch, and Continuous-Flow Mannich Reactions [J].
Alza, Esther ;
Rodriguez-Escrich, Carles ;
Sayalero, Sonia ;
Bastero, Amaia ;
Pericas, Miquel A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (39) :10167-10172
[4]   Assessing the suitability of 1,2,3-triazole linkers for covalent immobilization of chiral ligands:: Application to enantioselective phenylation of aldehydes [J].
Bastero, Amaia ;
Font, Daniel ;
Pericas, Miquel A. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2460-2468
[5]   A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly [J].
Baxendale, Ian R. ;
Deeley, Jon ;
Griffiths-Jones, Charlotte M. ;
Ley, Steven V. ;
Saaby, Steen ;
Tranmer, Geoffrey K. .
CHEMICAL COMMUNICATIONS, 2006, (24) :2566-2568
[6]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[7]   Controlling the formation of 1 out of 64 stereoisomers using organocatalysis [J].
Bertelsen, Soren ;
Johansen, Rasmus L. ;
Jorgensen, Karl Anker .
CHEMICAL COMMUNICATIONS, 2008, (26) :3016-3018
[8]   Improving solid-supported catalyst productivity by using simplified packed-bed microreactors [J].
Bogdan, Andrew R. ;
Mason, Brian P. ;
Sylvester, Kevin T. ;
McQuade, D. Tyler .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1698-1701
[9]   1,3-Dicarbonyl compounds in stereoselective domino and multicomponent reactions [J].
Bonne, Damien ;
Coquerel, Yoann ;
Constantieux, Thierry ;
Rodriguez, Jean .
TETRAHEDRON-ASYMMETRY, 2010, 21 (9-10) :1085-1109
[10]   A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].
Carlone, Armando ;
Cabrera, Silvia ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104