Insoluble polystyrene-bound bis(oxazoline): Batch and continuous-flow heterogeneous enantioselective glyoxylate-ene reaction

Tetrahedron Asymmetry

Volumn 15, Issue 20, 2004, Pages 3233-3244

  Mandoli, Alessandro ^a   Orlandi, Simonetta ^a   Pini, Dario ^a   Salvadori, Piero ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; GLYOXYLIC ACID DERIVATIVE; LIGAND; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 5144225548     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.08.015     Document Type: Article

References (53)

1. For reviews: A.K. Gosh, P. Mathiavanan, and J. Cappiello Tetrahedron: Asymmetry 9 1998 1 45
2. J.S. Johnson, and D.A. Evans Acc. Chem. Res. 33 2000 325 335
3. T.P. Yoon, and E.N. Jacobsen Science 299 2003 1691 1693
4. S. Crosignani, G. Desimoni, G. Faita, and P. Righetti Tetrahedron 54 1998 15721 15730
5. D.A. Evans, J.S. Johnson, and E.J. Olhava J. Am. Chem. Soc. 122 2000 1635 1649
6. J.M. Fraile, J.I. García, C.I. Herrerías, J.M. Mayoral, S. Gmough, and M. Vaultier Green Chem. 6 2004 93 98 and references cited therein
7. D.L. Davies, S.K. Kandola, and R.K. Patel Tetrahedron: Asymmetry 15 2004 77 80
8. For reviews: D. Rechavi, and M. Lemaire Chem. Rev. 102 2002 3467 3494
9. C. Jönsson, K. Hallman, H. Andersson, G. Stemme, M. Malkoch, E. Malström, A. Hult, and C. Moberg Bioorg. Med. Chem. Lett. 12 2002 1857 1861
10. Pioneering studies on the different approaches: J.M. Fraile, J.I. García, J.A. Mayoral, and T. Tarnai Tetrahedron: Asymmetry 8 1997 2089 2092 (ion exchange)
11. M.I. Burguete, J.M. Fraile, J.I. García, E. García-Verdugo, S.V. Luis, and J.A. Mayoral Org. Lett. 2 2000 2908 3905 (insoluble organic polymers)
12. M. Glos, and O. Reiser Org. Lett. 2 2000 2045 2048 (aza-box on soluble polymers)
13. D. Rechavi, and M. Lemaire Org. Lett. 3 2001 2493 2496 (inorganic surfaces)
14. J. Bayardon, and D. Sinou Tetrahedron Lett. 44 2003 1449 1451 (fluorous)
15. S. Orlandi, A. Mandoli, D. Pini, and P. Salvadori Angew. Chem., Int. Ed. 40 2001 2519 2521 (Mukaiyama)
16. A. Corma, H. García, A. Moussaif, M.J. Sabater, R. Zniber, and A. Redouane Chem. Commun. 2002 1058 1059 (Friedel-Crafts)
17. J. Gullick, S. Taylor, P. McMorna, D. Bethell, P.C. Bulman-Page, F.E. Hancock, F. King, and G.J. Hutchings J. Mol. Catal. A: Chem. 182-183 2002 571 575 (aziridination)
18. A. Mandoli, S. Orlandi, D. Pini, and P. Salvadori Chem. Commun. 2003 2466 2467 (cyclopropanation)
19. D.A. Evans, C.S. Burgey, N.A. Paras, T. Vojkovsky, and S.W. Tregay J. Am. Chem. Soc. 120 1998 5824 5825
20. D.A. Evans, S.W. Tregay, C.S. Burgey, N.A. Paras, and T. Vojkovsky J. Am. Chem. Soc. 122 2000 7936 7943
21. For an example of industrial application of the glyoxylate-ene reaction, see: H.U. Blaser, F. Spindler, and M. Studer Appl. Catal. A 221 2001 119 143
22. K. Mikami, and M. Terada E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis Vol. 3 1999 Springer Berlin 1143 1174 Chapter 32
23. Polymer supported BINOL's: Y.M.A. Yamada, M. Ichinohe, H. Takahashi, and S. Ikegami Tetrahedron Lett. 43 2002 3431 3434
24. T. Sekiguti, Y. Iizuka, S. Takizawa, D. Jayaprakash, T. Arai, and H. Sasai Org. Lett. 5 2003 2647 2650
25. Coordination polymers: S. Takizawa, H. Somei, D. Jayaprakash, and H. Sasai Angew. Chem., Int. Ed. 42 2003 5711 5714
26. H. Guo, X. Wang, and K. Ding Tetrahedron Lett. 45 2004 2009 2012
27. Other approaches: M. Johannsen, K.A. Jorgensen, X.-F. Zheng, Q.-S. Hu, and L. Pu J. Org. Chem. 64 1999 299 301 (Al-polymeric BINOL's)
28. J.H. Koh, A.O. Larsen, P.S. White, and M.R. Gagné Organometallics 21 2002 7 9 (Pt-diphosphine in imprinted polymers)
29. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, and M. Pitillo J. Org. Chem. 66 2001 3160 3166
30. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, and G. Pozzi Eur. J. Org. Chem. 2003 1191 1197
31. B. Simonelli, S. Orlandi, M. Benaglia, and G. Pozzi Eur. J. Org. Chem. 2004 2669 2673
32. For a discussion of the reaction mechanism: I. Morao, J.P. McNamara, and I.H. Hillier J. Am. Chem. Soc. 125 2003 628 629
33. N.A. Caplan, F.E. Hancock, P.C. Bulman Page, and G.J. Hutchings Angew. Chem., Int. Ed. 43 2004 1685 1688
34. J.M. Fraile, J.I. García, J.A. Mayoral, and T. Tarnai Tetrahedron: Asymmetry 9 1998 3997 4008
35. M.J. Fernandez, J.M. Fraile, J.I. García, J.A. Mayoral, M.I. Burguete, E. García-Verdugo, S.V. Luis, and M.A. Harmer Top. Catal. 13 2000 303 309
36. J.M. Fraile, J.I. Garcia, C.I. Herrerí-as, J.A. Mayoral, O. Reiser, A. Socuéllamos, and H. Werner Chem. Eur. J. 10 2004 2997 3005
37. S. Abramson, N. Bellocq, D. Brunel, M. Laspéras, and P. Moreau D.E. De Vos I.F.J. Vankelecom P. Jacobs Chiral Catalyst Immobilization and Recycling 2000 Weinheim Wiley-VCH Chapter 11, pp 261-282
38. E.J. Corey, N. Imai, and H.-Y. Zhang J. Am. Chem. Soc. 113 1991 728 729
39. Actually, the comonomer distribution in 12 has been estimated under the assumption of a styrene/DVB ratio similar to that of the feed, but this could be not the case. For a discussion on the complex polymerisation kinetic behavior in highly cross-linked polystyrene materials, see: A. Guyot, and M. Bartholin Prog. Polym. Sci. 8 1982 277 332
40. D.C. Sherrington Chem. Commun. 1998 2275 2286
41. R.P. Singh Bull. Soc. Chim. Fr. 134 1997 765 768
42. R.V. Law, D.C. Sherrington, and C.E. Snape Macromolecules 30 1997 2868 2875
43. J.R. Millar, D.G. Smith, W.E. Marr, and T.R.E. Kressman J. Chem. Soc. 1963 218 225
44. I.M. Abrams, and J.R. Millar React. Funct. Polym. 35 1997 7 22
45. It is however worth noting that the results did not change for samples dried from methanol. Compare Ref. a
46. Leading references in the field of enantioselective transformations: P. Hodge, D.W.L. Sung, and P.W. Stratford J. Chem. Soc., Perkin Trans. 1 1999 2335 2342
47. M.I. Burguete, E. García-Verdugo, M.J. Vicent, S.V. Luis, H. Pennemann, N.G. von Keyserling, and J. Martens Org. Lett. 4 2002 3947 3950
48. A.M. Hafez, A.E. Taggi, and T. Lectka Chem. Eur. J. 8 2002 4115 4119
49. This experimental arrangement has been used before for the evaluation of supported enantioselective catalysts, generally with silica gel or monolith packings. See for example: D.A. Annis, and E.N. Jacobsen J. Am. Chem. Soc. 121 1999 4147 4154
50. B. Altava, M.I. Burguete, J.M. Fraile, J.I. García, S.V. Luis, J.A. Mayoral, and M.J. Vicent Angew. Chem., Int. Ed. 39 2000 1503 1506
51. C. García, T. Martín, and V.S. Martín J. Org. Chem. 66 2001 1420 1428
52. M.R. Johnson, and Y. Kishi Tetrahedron Lett. 1979 4347 4350
53. S. Weigand, and R. Brueckner Synthesis 1996 475 482