Asymmetric catalysis induced by the substrate itself

Coordination Chemistry Reviews

Volumn 248, Issue 21-24, 2004, Pages 2193-2200

  Kalck, Philippe ^a   Urrutigoïty, Martine ^a  

^a Laboratoire de Catalyse Chimie Fine et Polymeres   (France)

Author keywords

Asymmetric induction; Catalysis; Chiral substrate; Stereodifferentiation

Indexed keywords

BETA PINENE; CARBON; LIGAND; METAL; STEROID; TERPENE; TERPINEOL;

ALKYLATION; ANNULATION REACTION; ATOM; CARBONYLATION; CATALYSIS; CHIRALITY; DIHYDROXYLATION; HYDROFORMYLATION; REVIEW; STEREOCHEMISTRY;

EID: 9644310429     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2004.05.001     Document Type: Review

References (56)

1. Pasteur L. CR Acad. Sci. Paris. 26:1848;535
2. quoted by H.B. Kagan, C.R. Acad. Sci. Paris t. 322 (Serie II b) (1996) 131.
3. Knowles W.S., Sabacky M.J., Vineyard B.I., Weinkauff D.J. J. Am. Chem. Soc. 97:1975;2567
4. E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis I, II, III, Springer, Berlin, Heidelberg, 1999.
5. Kolodiazhnyi O.I. Tetrahedron. 59:2003;5953
6. Miyashita A., Yasuda A., Takaya H., Ito K., Souchi T., Noyori R. J. Am. Chem. Soc. 102:1980;7932
7. I. Ojima, Catalytic Asymmetric Synthesis, second ed., Wiley-VCH, New York, 2000.
8. Muniz K., Bolm C. Chem. Eur. J. 6:2000;2309
9. Blaser H.U., Malan C., Pugin B., Spindler F., Steiner H., Studer M. Adv. Synth. Catal. 345:2003;103. and most of the papers published in this special issue
10. Y. Izumi, A. Tai, Stereodifferentiating Reactions, Academic Press, New York, 1977.
11. Lenoble G., Naigre R., Chenal T., Urrutigoïty M., Daran J.C., Kalck Ph. Tetrahedron: Asymm. 10:1999;929
12. Lacaze-Dufaure C., Lenoble G., Urrutigoïty M., Gorrichon J.P., Mijoule C., Kalck Ph. Tetrahedron: Asymm. 12:2001;185
13. Lenoble G., Lacaze-Dufaure C., Urrutigoïty M., Mijoule C., Kalck Ph. Eur. J. Inorg. Chem. 4:2004;791
14. Dias A.O., Augusti R., Dos Santos E.N., Gusevskaya E.V. Tetrahedron Lett. 38:1997;41
15. Azzaroni F., Biscarini P., Bordoni S., Longoni G., Venturini E. J. Organomet. Chem. 508:1996;59
16. Garland M., Horvath I.T., Bor G., Pino P. J. Organomet. Chem. 358:1988;C 17
17. Garland M., Pina P. Organometallics. 9:1990;143
18. Gusevskaya E.V., dos Santos E.N., Augusti R., Foca C.M., Dias A.O. J. Mol. Catal. A. 152:2000;15
19. Barros H.J.V., Ospina M.L., Arguello E., Rocha W.R., Gusevskaya E.V., Dos Santos E.N. J. Organomet. Chem. 671:2003;150
20. Kalck Ph., Sirol S. New. J. Chem. 21:1997;1129
21. Cristea I., Kozma E., Batiu C. Tetrahedron: Asymm. 13:2002;915
22. Brodi A.M.H., Njar V.C.O. Steroids. 65:2000;171
23. Skoda-Földes R., Kollar L., Arcadi A. J. Mol. Catal. A. 101:1995;37
24. Freixa Z., Pereira M.M., Bayon J.C., Silva A.M.S., Salvador J.A.R., Beja A.M., Paixao J.A., Ramos M. Tetrahedron: Asymm. 12:2001;1083
25. Beal P.F., Rebenstorf M.A., Pike J.E. J. Am. Chem. Soc. 81:1959;1231
26. Evans P.A., Robinson J.E. J. Am. Chem. Soc. 123:2001;4609
27. Ranade V.S., Prins R. J. Catal. 185:1999;479
28. Besson M., Blanc B., Champelet M., Gallezot P., Nasar K., Pinel C. J. Catal. 170:1997;254
29. Besson M., Gallezot P., Neto S., Pinel C. Chem. Commun. 14:1998;1432
30. Besson M., Delbecq F., Gallezot P., Neto S., Pinel C. Chem. Eur. J. 6:2000;949
31. Ranade V.S., Consiglio G., Prins R. Catal. Lett. 58:1999;71
32. Hegedus L., Hada V., Tungler A., Mathé T., Szepesy L. Appl. Catal. A: General. 201:2000;107
33. Kukula P., Prins R. J. Catal. 217:2003;240
34. de la Rosa J.C., Diaz N., Carretero J.C. Tetrahedron Lett. 41:2000;4107
35. Rebiere F., Samuel O., Ricard L., Kagan H.B. J. Org. Chem. 56:1991;5991
36. Yu K., Li H., Watson E.J., Virkaitis K.L., Carpenter G.B., Sweigart B.A. Organometallics. 20:2001;3550
37. Dubs M., Dieks H., Günther W., Köheristzsch M., Poppitz W., Schönecker B. Tetrahedron Lett. 43:2002;2499
38. B. Breit, Liebigs Ann. (1997) 1841.
39. B. Breit, Chem. Comm. (1997) 591.
40. Breit B., Zahn S.Z. Tetrahedron Lett. 39:1998;1901
41. Breit B., Zahn S.Z. Polyhedron. 19:2000;513
42. B. Breit, P. Demel, A. Gebert, Chem. Commun. (2004) 114.
43. Breit B., Duber M., Harms K. Chem. Eur. J. 5:1999;2819
44. Davis M.E. Topics Catal. 25:2003;3. and references cited herein
45. Vayner G., Houk K.N., Sun Y.K. J. Am. Chem. Soc. 126:2004;199
46. Studer M., Blaser H.U., Exner C. Adv. Synth. Catal. 345:2003;45
47. Van Der Wall J.C., Van Becklum H., Vital J.M. J. Mol. Catal. A. 105:1996;185
48. Huffman M.A., Reider P.J. Tetrahedron Lett. 40:1999;831
49. Guidotti M., Conti L., Fusi A., Ravasio N., Psaro R. J. Mol. Catal. A. 182-183:2002;151
50. Jacob R.G., Perin G., Loi L.N., Pinno C.S., Lenardao E.J. Tetrahedron Lett. 44:2003;3605
51. Gini F., Del Moro F., Macchia F., Pinescho M. Tetrahedron Lett. 44:2003;8559
52. Besson M., Gallezot P., Neto S., Pinet C. Tetrahedron: Asymm. 11:2000;1809
53. Blaser H.U., Indolese A., Schnyder A., Steiner H., Studer M. J. Mol. Catal. A. 173:2001;3
54. Blackmond D.G. Adv. Synth. Catal. 344:2002;156
55. Buono F.G., Iwamura H., Blackmond D.G. Angew. Chem. 116:2004;2151
56. Noyori R. Adv. Synth. Catal. 345:2003;15