A solid-supported organocatalyst for highly stereoselective, batch, and continuous-flow mannich reactions

Chemistry - A European Journal

Volumn 15, Issue 39, 2009, Pages 10167-10172

  Alza, Esther ^a   Rodríguez Escrich, Carles ^a   Sayalero, Sonia ^a   Bastero, Amaia ^a   Pericàs, Miquel A ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Aldehydes; Asymmetric catalysis; Flow reactors; Mannich reactions; Organocatalysis

Indexed keywords

ALDEHYDES; CATALYSIS; HYDROXYPROLINE; KETONES; MICROWAVE IRRADIATION; POLYSTYRENES; RESINS; STEREOSELECTIVITY;

ASYMMETRIC CATALYSIS; CONTINUOUS SYNTHESIS; EXPERIMENTAL PROTOCOLS; FLOW REACTORS; MANNICH REACTIONS; ORGANOCATALYSIS; POLYMERIC BACKBONE; SIX-MEMBERED RINGS;

CATALYST ACTIVITY;

EID: 70349653333     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901310     Document Type: Article

References (55)

1. S. J. Lippard, Chem. Eng. News 2000, 78, 64.
2. a) A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley VCH, Weinheim, 2005;
3. b) P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007;
4. c) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232;
5. Angew. Chem. Int. Ed. 2008, 47, 6138.
6. For reviews, see: a) D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs, Chiral Catalyst Immobilization and Recycling, Wiley-VCH, Weinheim, 2000;
7. b) K. Ding, Y Uozumi, Handbook of Asymmetric Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2008;
8. c) M. Gruttadauria, F. Giacalone, R. Noto, Chem. Soc. Rev. 2008, 37, 1666.
9. a) D. Font, C. Jimeno, M. A. Pericàs, Org. Lett. 2006, 8, 4653;
10. b) D. Font, A. Bastero, S. Sayalero, C. Jimeno, M. A. Pericàs, Org. Lett. 2007, 9, 1943;
11. c) D. Font, S. Sayalero, A. Bastero, C. Jimeno, M. A. Pericàs, Org. Lett. 2008, 10, 337;
12. d) E. Alza, X. C. Cambeiro, C. Jimeno, M. A. Pericàs, Org. Lett. 2007, 9, 3717.
13. Pioneering three-component organocatalytic Mannich reaction: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
14. b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827; for recent reviews on organocatalytic Mannich reactions, see:
15. c) J. M. M. Verkade, J. C. v. H. Lieke, P. J. L. M. Quadflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29;
16. d) A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797.
17. For recent reviews, see: a) C. Wiles, P. Watts, Eur. J. Org. Chem. 2008, 1655;
18. b) B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Chem. Rev. 2007, 107, 2300;
19. c) F. Cozzi, Adv. Synth. Catal. 2006, 348, 1367;
20. d) A. Kirschning, W. Solodenko, K. Mennecke, Chem. Eur. J. 2006, 12, 5972.
21. For recent advances in flow chemistry, see: a) S. Saaby, K. R. Knudsen, M. Ladlow, S. V. Ley, Chem. Commun. 2005, 2909;
22. b) I. R. Baxendale, J. Deeley, C. M. Griffiths-Jones, S. V. Ley, S. Saaby, G. K. Tranmer, Chem. Commun. 2006, 2566;
23. c) A. R. Bogdan, B. P. Mason, K. T. Sylvester, D. T. MacQuade, Angew. Chem. 2007, 119, 1728;
24. Angew. Chem. Int. Ed. 2007, 46, 1698;
25. d) C. D. Smith, I. R. Baxendale, S. Lanners, J. J. Hayward, S. C. Smith, S. V. Ley, Org. Biomol. Chem. 2007, 5, 1559.
26. a) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, J. Am. Chem. Soc. 2002, 124, 1842;
27. b) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas, J. Org. Chem. 2003, 68, 9624;
28. c) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urashima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805;
29. Angew. Chem. Int. Ed. 2003, 42, 3677;
30. d) I. Ibrahem, J. Casas, A. Córdova, Angew. Chem. 2004, 116, 6690;
31. Angew. Chem. Int. Ed. 2004, 43, 6528;
32. e) J.W. Yang, M. Stadler, B. List, Angew. Chem. 2007, 119, 615;
33. Angew. Chem. Int. Ed. 2007, 46, 609;
34. f) N. Utsumi, H. Zhang, F. Tanaka, C. F. Barbas, Angew. Chem. 2007, 119, 1910;
35. Angew. Chem. Int. Ed. 2007, 46, 1878;
36. g) J. W. Yang, C. Chandler, M. Stadler, D. Kampen, B. List, Nature 2008, 452, 453;
37. h) C. Chandler, P. Galzerano, A. Michrowska, B. List, Angew. Chem. 2009, 121, 2012;
38. Angew. Chem. Int. Ed. 2009, 48, 1978.
39. a) T. Razzaq, J. M. Kremsner, C. O. Kappe, J. Org. Chem. 2008, 73, 6321;
40. b) A. de La Hoz, A. Diaz-Ortiz, A. Moreno, Chem. Soc. Rev. 2005, 34, 164.
41. These recycling experiments show the results obtained in three consecutive runs. After each run, the reaction mixture was filtered and washed with DMF and the solid-supported catalyst was directly reused.
42. The residence time was determined by pumping a solution of methyl red through the system and measuring the time elapsed between the first contact of the dye with the resin and the moment when red color appears at the column output.
43. A. Odedra, P. H. Seeberger, Angew. Chem. 2009, 121, 2737;
44. Angew. Chem. Int. Ed. 2009, 48, 2699.
45. For some examples, see: a) M. A. Pericàs, C. I. Herrerías, L. Solà, Adv. Synth. Catal. 2008, 350, 927;
46. b) W. Solodenko, G. Jas, U. Kunz, A. Kirschning, Synthesis 2007, 583;
47. c) F. Bonfils, I. Cazaux, P. Hodge, C. Caze, Org. Biomol. Chem. 2006, 4, 493;
48. d) P. Stephenson, B. Kondor, P. Licence, K. Scovell, S. K. Ross, M. Poliakoff, Adv. Synth. Catal. 2006, 348, 1605.
49. K. Kondo, T. Yamano, K. Takemoto, Makromol. Chem. 1985, 186, 1781.
50. max (mmol ligand per gram resin), the maximal ligand functionalization level, is calculated as described in the following: A. Vidal-Ferran, N Bampos, A. Moyano, M. A. Pericas, A. Riera, J. K. M. Sanders, J. Org. Chem. 1998, 63, 6309.
51. J. A. Cobb, D. M. Shaw, D. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84.
52. A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, J. Am. Chem. Soc. 2002, 124, 1866.
53. A. Córdova, C. F. Barbas, Tetrahedron Lett. 2003, 44, 1923.
54. J. A. Cobb, D. M. Shaw, S. V. Ley, Synlett 2004, 558.
55. W. Wang, J. Wang, H. Li, Tetrahedron Lett. 2004, 45, 7243.