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
    Alza, Esther
    Cambeiro, Xacobe C.
    Jimeno, Ciril
    Pericas, Miquel A.
    [J]. ORGANIC LETTERS, 2007, 9 (19) : 3717 - 3720
  • [2] A Highly Selective, Polymer-Supported Organocatalyst for Michael Additions with Enzyme-Like Behavior
    Alza, Esther
    Pericas, Miquel A.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3051 - 3056
  • [3] A Solid-Supported Organocatalyst for Highly Stereoselective, Batch, and Continuous-Flow Mannich Reactions
    Alza, Esther
    Rodriguez-Escrich, Carles
    Sayalero, Sonia
    Bastero, Amaia
    Pericas, Miquel A.
    [J]. 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
    Bastero, Amaia
    Font, Daniel
    Pericas, Miquel A.
    [J]. 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
    Baxendale, Ian R.
    Deeley, Jon
    Griffiths-Jones, Charlotte M.
    Ley, Steven V.
    Saaby, Steen
    Tranmer, Geoffrey K.
    [J]. 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
    Bertelsen, Soren
    Johansen, Rasmus L.
    Jorgensen, Karl Anker
    [J]. CHEMICAL COMMUNICATIONS, 2008, (26) : 3016 - 3018
  • [8] Improving solid-supported catalyst productivity by using simplified packed-bed microreactors
    Bogdan, Andrew R.
    Mason, Brian P.
    Sylvester, Kevin T.
    McQuade, D. Tyler
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1698 - 1701
  • [9] 1,3-Dicarbonyl compounds in stereoselective domino and multicomponent reactions
    Bonne, Damien
    Coquerel, Yoann
    Constantieux, Thierry
    Rodriguez, Jean
    [J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (9-10) : 1085 - 1109
  • [10] A new approach for an organocatalytic multicomponent domino asymmetric reaction
    Carlone, Armando
    Cabrera, Silvia
    Marigo, Mauro
    Jorgensen, Karl Anker
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) : 1101 - 1104