Enantioselective catalysis using heterogeneous bis(oxazoline) ligands: Which factors influence the enantioselectivity?

Chemical Reviews

Volumn 102, Issue 10, 2002, Pages 3467-3494

  Rechavi, Dalit ^a   Lemaire, Marc ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE CATALYSIS;

CHEMICAL BONDS; COMPLEXATION; DENDRIMERS; DERIVATIVES; ION EXCHANGE; ISOMERS; SOLVENTS; SUBSTITUTION REACTIONS; SUBSTRATES;

CATALYSIS;

EID: 0036811192     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr020008m     Document Type: Article

References (98)

1. For a review of bis(oxazoline) ligands see Ghosh, A.K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
2. Bolm, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 542.
3. Jannes, G.; Dubois, V.; Eds. Chiral Reactions in Heterogeneous Catalysis; Proceedings of the First European Symposium on Chiral Reactions in Heterogeneous Catalysis, held October 25-26, 1993, in Brussels, Belgium; Plenum Press: New York, 1995.
4. Kragl, U.; Dwars, T. Trends Biotechnol. 2001, 19, 442.
5. Clapham, B.; Reger, T.S.; Janda, K.D. Tetrahedron 2001, 57, 4637.
6. Chiral Catalyst Immobilization and Recycling; 1st ed.; De Vos, D.E.; Vankelecom, I.F.J.; Jacobs, P.A., Eds.; Wiley-VCH: Weinheim, 2000.
7. Sheldon, R.A. Chem. Ind. (London) 1992, 903.
8. Chow, H.-F.; Mak, C.C. J. Org. Chem. 1997, 62, 5116.
9. Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 5239.
10. For a recent review of cyclopropanation reactions see Singh, V.K.; Datta Gupta, A.; Sekar, G. Synthesis 1997, 137.
11. For a recent review of cyclopropanation reactions see Doyle, M.P.; Protopopova, M.N. Tetrahedron 1998, 54, 7919.
12. For a specific review of cyclopropanation using polynitrogenated supported ligands see Adrián, F.; Burguete, M.I.; Fraile, J.M.; García, J.I.; García, J.; García Espana, E.; Luis, S.V.; Mayoral, J.A.; Royo, A.J.; Sanchez, M.C. Eur. J. Inorg. Chem. 1999, 2347.
13. For acis selective ligand see Bachmann, S.; Furler, M.; Mezzetti, A. Organometallics 2001, 20, 2102.
14. Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv. Chim. Acta 1988, 71, 1553.
15. Lowenthal, R.E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
16. Evans, D.A.; Woerpel, K.A.; Hinman, M.M.; Faul, M.M. J. Am. Chem. Soc. 1991, 113, 726.
17. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
18. Fraile, J.M.; García, J.I.; Martinez Merino, V.; Mayoral, J.A.; Salvatella, L. J. Am. Chem. Soc. 2001, 123, 7616.
19. Rasmussen, T.; Jensen, J.F.; Ostergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.O. Chem. Eur. J. 2002, 8, 177.
20. Díaz-Requejo, M.M.; Belderrain, T.R.; Nicasio, M.C.; Prieto, F.; Perez, P.J. Organometallics 1999, 18, 2601.
21. Fraile, J.M.; García, J.I.; Mayoral, J.A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089.
22. Fraile, J.M.; García, J.I.; Mayoral, J.A.; Tarnai, T. Tetrahedron: Asymmetry 1998, 9, 3997.
23. Fraile, J.M.; García, J.I.; Mayoral, J.A.; Tarnai, T.; Harmer, M.A. J. Catal. 1999, 186, 214.
24. Alonso, P.J.; Fraile, J.M.; García, J.; García, J.I.; Martinez, J.I.; Mayoral, J.A.; Sanchez, M.C. Langmuir 2000, 16, 5607.
25. Fernandez, A.I.; Fraile, J.M.; García, J.I.; Herrerias, C.I.; Mayoral, J.A.; Salvatella, L. Catal. Commun. 2001, 2, 165.
26. Clark, J.H.; Kybett, A.P.; Macquarrie, D.J. Supported Reagents Preparation, Analysis, and Applications; VCH Publishers Inc.; VCH Verlagsgesellschaft mbH.; VCH Publishers (UK) Ltd.: New York; Weinheim; Cambridge, 1992; p 106.
27. Skordilis, C.S.; Pomonis, P.J. J. Mol. Catal. A: Chem. 1995, 107, 191.
28. Fraile, J.M.; García, J.I.; Mayoral, J.A.; Tarnai, T. Tetrahedron: Asymmetry 1998, 9, 3997.
29. Fraile, J.M.; García, J.I.; Mayoral, J.A.; Tarnai, T. J. Mol. Catal. A: Chem. 1999, 144, 85.
30. Olah, G.A.; Iyer, P.S.; Prakash, G.K.S. Synthesis 1986, 513.
31. Burguete, M.I.; Fraile, J.M.; García, J.I.; GarcíaVerdugo, E.; Luis, S.V.; Mayoral, J.A. Org. Lett. 2000, 2, 3905.
32. Altava, B.; Burguete, M.I.; Fraile, J.M.; García, J.I.; Luis, S.V.; Mayoral, J.A.; Vicent, M.J. Angew. Chem., Int. Ed. Engl. 2009, 39, 1503.
33. Burguete, M.I.; Fraile, J.M.; García, J.I.; García-Verdugo, E.; Herrerias, C.I.; Luis, S.V.; Mayoral, J.A. J. Org. Chem. 2001, 66, 8893.
34. Fernández, M.J.; Fraile, J.M.; García, J.I.; Mayoral, J.A.; Burguete, M.I.; García-Verdugo, E.; Luis, S.V.; Harmer, M.A. Topics Catal. 2000, 13, 303.
35. Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Perichs, M.A.; Riera, A.; Sanders, J.K.M. J. Org. Chem. 1998, 63, 6309.
36. Oguni, N.; Matsuda, Y.; Maneko, T. J. Am. Chem. Soc. 1988, 110, 7877.
37. Grubbs, R.; Lau, C.P.; Cukier, R.; Jr., C.B. J. Am. Chem. Soc. 1977, 99, 4517.
38. Pugin, B. J. Mol. Catal. A: Chem. 1996, 107, 273.
39. Clarke, R.J.; Shannon, I.J. Chem. Commun. 2001, 1936.
40. Kresge, C.T.; Leonowicz, M.E.; Roth, W.J.; Vartuli, J.C.; Beck, J.S. Nature (London) 1992, 359, 710.
41. Zhao, D.; Yang, P.; Huo, Q.; Chmelka, B.F.; Stucky, G.D. Curr. Opin. Solid State Mater. Sci. 1998, 3, 111.
42. Maschmeyer, T. Curr. Opin. Solid State Mater. Sci. 1998, 3, 71.
43. Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045.
44. Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pitillo, M. J. Org. Chem. 2001, 66, 3160.
45. Denmark, S.E.; Nakajima, N.; Nicaise, O.J.-C.; Faucher, A.M.; Edwards, J.P. J. Org. Chem. 1995, 60, 4884.
46. Evans, D.A.; Peterson, G.S.; Johnson, J.S,; Barnes, D.M.; Campos, K.R,; Woerpel, K.A. J. Org. Chem. 1998, 63, 4541.
47. Fraile, J.M.; García, J.I.; Herrerias, C.I.; Mayoral, J.A.; Carrie, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891.
48. Dias, L.C. Curr. Org. Chem. 2000, 4, 305.
49. Mikami, K.; Terada, M. Comprehensive Asymmetric Catalysis I-III 1999, 3, 1143.
50. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967.
51. Johannsen, M.; Jorgensen, K.A. J. Org. Chem. 1995, 60, 5757.
52. Evans, D.A.; Tregay, S.W.; Burgey, C.S.; Paras, N.A.; Vojkovsky J. Am. Chem. Soc. 2000, 122, 7936.
53. Evans, D.A.; Miller, S.J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559.
54. Corey, E.J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728.
55. Corey, E.J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807.
56. Davies, I.W.; Gerena, L.; Castonguay, L.; Senanayake, C.H.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Chem. Soc., Chem. Commun. 1996, 1753.
57. Davies, I.W.; Deeth, R.J.; Larsen, R.D.; Reider, P.J. Tetrahedron Lett. 1999, 40, 1233.
58. Evans, D.A.; Miller, S.J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460.
59. Desimoni, G.; Faita, G.; Righetti, P.P. Tetrahedron Lett. 1996, 37, 3027.
60. For a similar effect in 1,3-dipolar cycloadditions see: Gothelf, K.V,; Hazell, R.G.; Jorgeusen, K.A. J. Org. Chem. 1998, 63, 5483.
61. Ghosh, A.K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687.
62. Ghosh, A.K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815.
63. Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721.
64. Evans, D.A.; Johnson, J.S.; Olhava, E.J. J. Am. Chem. Soc. 2000, 122, 1635.
65. Fraile, J.M.; García, J.I.; Harmer, M.A.; Herrerias, C.I.; Mayoral, J.A. J. Mol. Catal. A: Chem. 2001, 165, 211.
66. Gerstberger, G.; Anwander, R. Microporous Mesoporous Mater. 2001, 44 Special Issue. SI, 303.
67. Hallman, K.; Moberg, C. Tetrahedron:Asymmetry 2001, 12, 1475.
68. Rechavi, D.; Lemaire, M. J. Mol. Catal. A: Chem. 2002, 182-183, 239.
69. Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-I.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D.P. J. Am. Chem. Soc. 1998, 120, 3074.
70. Rechavi, D.; Lemaire, M. Org. Lett. 2001, 3, 2493.
71. Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623.
72. Manickam, G.; Sundararajan, G. Tetrahedron: Asymmetry 1999, 10, 2913.
73. Park, J.K,; Kim, S.-W.; Hyeon, T.; Kim, B.M. Tetrahedron: Asymmetry 2001, 12, 2931.
74. Schmidt-Winkel, P.W.W.L., Jr.; Zhao, D.; Yang, P.; Chmelka, B.F.; Stucky, G.D. J. Am. Chem. Soc. 1999, 121, 254.
75. von Matt, P.; Lloyd-Jones, G.C.; Minidis, A.B.E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zhender, M.; Ruegger, H.; Pregosin, P.S. Helv. Chim. Acta 1995, 78, 265.
76. Hallman, K.; Moberg, C. Tetrahedron:Asymmetry 2001, 12, 1475.
77. Jacobsen, E.N. Comprehensive Asymmetric Catalysis I-III 1999, 2, 607.
78. Evans, D.A.; Faul, M.M.; Bilodeau, M.T.; Anderson, B.A.; Barnes, D.M. J. Am. Chem. Soc. 1993, 115, 5328.
79. Evans, D.A.; Bilodeau, M.T.; Faul, M.M. J. Am. Chem. Soc. 1994, 116, 2742.
80. Li, Z.; Quan, R.W.; Jacobsen, E.N. J. Am. Chem. Soc. 1995, 117, 5889.
81. Langham, C.; Piaggio, P.; Bethell, D.; Lee, D.F.; McMorn, P.; Page, P.C.B.; Willock, D.J.; Sly, C.; Hancock, F.E.; King, F.; Hutchings, G. J. Chem. Commun. 1998, 1601.
82. Hutchings, G. J. Chem. Commun. 1999, 301.
83. Langham, C.; Bethell, D.; Lee, D.E,; McMorn, P.; Page, P.C.B.; Willock, D.J.; Sly, C.; Hancock, F.E.; King, F.; Hutchings, G. J. Appl. Catal. A: General 1999, 182, 85.
84. Bethell, D.; Hutchings, G.J.; Langham, C.; Page, P.C.B.; Lee, D.F. (Imperial Chemical Industries Plc, UK) U.S. Patent 5,852,205, 1998.
85. Bethell, D.; Hutchings, G.J.; Langham, C.; Page, P.C.B.; Lee, D.F. (Imperial Chemical Industries Plc, UK) European Patent EP 0831086A1, 1998.
86. For another example using a zeolite see: Feast, S.; Bethell, D.; Page, P.C.B.; King, F.; Rochester, C.H.; Siddiqui, M.R.H.; Willock, D.J.; Hutchings, G.J. J. Chem. Soc., Chem. Commun. 1995, 2409.
87. For another example using an MCM see Hutchings, G.J.; Langham, C.; Piaggio, P.; Taylor, S.; McMorn, P.; Willock, D.J.; Bethell, D.; Page, P.C.B,; Sly, C.; Hancock, F.; King, F. Special Publication - Royal Society of Chemistry 2001, 266, 94.
88. Wells, P.B.; Wilkinson, A.G. Topics Catal. 1998, 5, 39.
89. Simons, K.E.; Wang, G.; Hienz, T.; Giger, T.; Mallat, T.; Pfaltz, A.; Baiker, A. Tetrahedron: Asymmetry 1995, 6, 505.
90. Blaser, H.U.; Jalett, H.P.; Monti, D.M.; Baiker, A.; Wehrli, J.T. Stud. Surf. Sci. Catal. 1991, 67, 147.
91. Langham, C.; Taylor, S.; Bethell, D.; McMorn, P.; Page, P.C.B.; Willock, D.J.; Sly, C.; Hancock, F.E.; King, F.; Hutchings, G.J. J. Chem. Soc., Perkin Trans. 2 1999, 1043.
92. Traa, Y.; Murphy, D.M.; Farley, R.D.; Hutchings, G. J. Phys. Chem. Chem. Phys. 2001, 3, 1073.
93. Taylor, S.; Gullick, J.; McMorn, P.; Bethell, D.; Page, P.C.B.; Hancock, F.E.; King, F.; Hutchings, G.J. J. Chem. Soc., Perkin Trans. 2 2001, 1714.
94. Taylor, S.; Gullick, J.; McMorn, P.; Bethell, D.; Page, P.C.B.; Hancock, F.E.; King, F.; Hutchings, G.J. J. Chem. Soc., Perkin Trans. 2 2001, 1724.
95. Gullick, J.; Taylor, S.; Kerton, O.; McMorn, P.; King, F.; Hancock, F.E.; Bethell, D.; Page, P.C.B.; hutchings, G. J. Catal. Lett. 2001, 75, 151.
96. Orlandi, S.; Mandoli, A.; Pini, D.; Salvadori, P. Angew. Chem., Int. Ed. Engl. 2001, 40, 2519.
97. Groger, H.; Vogl, E.M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137.
98. Carreira, E.M. Comprehensive Asymmetric Catalysis I-III 1999, 3, 997.