Catalytic asymmetric hydrogenation of α-ketoesters and quinoline using electronically enriched BINAP

Tetrahedron Asymmetry

Volumn 18, Issue 19, 2007, Pages 2305-2312

  Jahjah, Mohamad ^a   Alame, Mohamad ^a   Pellet Rostaing, Stéphane ^a   Lemaire, Marc ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; IRIDIUM; LIGAND; PHOSPHINE DERIVATIVE; QUINOLINE; QUINOLINE DERIVATIVE; RUTHENIUM;

ARTICLE; ASYMMETRIC CATALYSIS; COMPARATIVE STUDY; DERIVATIZATION; ELECTRONICS; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; QUANTUM YIELD; SUBSTITUTION REACTION; SUPRAMOLECULAR CHEMISTRY;

EID: 35348878469     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.09.022     Document Type: Article

References (54)

1. Trost B.M. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5348
2. Hanessian S. Total Synthesis of Natural Products: The Chiron Approach (1983), Pergamon Press, New York
3. Koh K., Ben R.N., and Durst T. Tetrahedron Lett. 34 (1993) 4473
4. Jian-Xin G., Zu-Li L., and Guo-Qiang L. Tetrahedron 49 (1993) 5805
5. Xiang Y.B., Snow K., and Belley M. J. Org. Chem. 58 (1993) 993
6. Wang C.-J., Sun X., and Zhang X. Synlett (2006) 1169
7. Cederbaum F., Lamberth C., Malan C., Naud F., Spindler F., Studer M., and Blaser H.-U. Adv. Synth. Catal. 346 (2004) 842 and references cited therein
8. Pasquier C., Naili S., Mortreux A., Agbossou F., Pelinski L., Brocard J., Eilers J., Reiner I., Peper V., and Martens J. Organometallics 19 (2000) 5723
9. Blaser H.-U., Jalett H.-P., Garland M., Studer M., Thies H., and Wirthtijani A. J. Catal. 173 (1998) 282
10. Schurch M., Schwalm O., Mallat T., Weber J., and Baiker A. J. Catal. 169 (1997) 275 and references cited therein
11. Wang G.-Z., Mallat T., and Baiker A. Tetrahedron: Asymmetry 8 (1997) 2133
12. Carpentier J.F., and Mortreux A. Tetrahedron: Asymmetry 8 (1997) 1083
13. Blaser H.-U., Jalett H.-P., and Spindler F. J. Mol. Catal. 107 (1996) 85
14. Chiba T., MJyashita A., Nohira H., and Takaya H. Tetrahedron Lett. 34 (1993) 2351
15. Qiu L., Kwong F.Y., Wu J., Lam W.H., Chan S., Yu W.-Y., Li Y.-M., Guo R., Zhou Z., and Chan A.S.C. J. Am.Chem. Soc. 128 (2006) 5955
16. Dupart de Paule S., Severine J., Ratovelomanana-Vidal V., Genet J.P., Champion N., and Dellis P. Eur. J. Org. Chem. 10 (2003) 1931
17. Genet J.P., Pinel C., Mallart S., Juge S., Cailhol N., and Laffitte J.A. Tetrahedron Lett. 33 (1992) 5343
18. Genêt J.P., Pinel C., Ratovelomanana-Vidal V., Mallart S., Pfister X., Bischoff L., Cano De Andrade M.C., Darses S., Galopin C., and Laffitte J.A. Tetrahedron: Asymmetry 5 (1994) 675
19. Barton D.H., Nakanishi K., and Meth-Cohn O. Comprehensive Natural Products Chemistry Vols. 1-9 (1999), Elsevier, Oxford
20. Katritzky A.R., Rachwal S., and Rachwal B. Tetrahedron 52 (1996) 15031
21. Rylander P.N. Catalytic Hydrogenation in Organic Synthesis (1979), Academic Press, New York p 175
22. Blaser H.-U., Malan C., Pugin B., Splindler F., Steiner H., and Studer M. Adv. Synth. Catal. 345 (2003) 103
23. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029
24. Lin G.O., Li Y.M., and Chan A.S.C. Principles and Applications of Asymmetric Synthesis (2001), Wiley-Interscience, New York
25. Henschke J.P., Burk M.J., Malan C.G., Herzberg D., Peterson J.A., Wildsmith A.J., Cobley C.J., and Casy G. Adv. Synth. Catal. 345 (2003) 300
26. Kuwano R., Kaneda K., Ito T., Sato K., Kurokawa T., Karube D., and Ito Y. Org. Lett. 6 (2004) 2213
27. Reetz M.T., and Li X. Chem. Commun. (2006) 2159
28. Lam K.H., Xu L., Feng L., Fan Q.-H., Lam F.L., Lo W.-H., and Chan A.S.C. Adv. Synth. Catal. 347 (2005) 1755
29. Wang W., Lu S., Yang Y., Han X., and Zhou Y. J. Am. Chem. Soc. 125 (2003) 10536
30. Yang P., and Zhou Y. Tetrahedron: Asymmetry 15 (2004) 2222
31. Lu S., Han X., and Zhou Y. Adv. Synth. Catal. 346 (2004) 909
32. Lu S., Wang Y., Han X., and Zhou Y. Angew. Chem., Int. Ed. 45 (2006) 2260
33. Tang W.-J., Zhu S.-F., Xu L.-J., Zhou Q.-L., Fan Q.-H., Zhou H.-F., Lam K., and Chan A.S.C. Chem. Commun. (2007) 613
34. Mashima K., Kusano K., Sato N., Matsumara Y., Nozaki K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., and Takaya H. J. Chem. Soc., Chem. Commun. 9 (1991) 609
35. Jeulin S., Duprat de Paule S., Ratovelomanana-Vidal V., Genêt J.P., Champion N., and Dellis P. Angew. Chem., Int. Ed. 43 (2004) 320
36. Murata M., Morimoto T., and Achiwa K. Synlett (1991) 827
37. Benincori T., Piccolo O., Rizzo S., and Sannicolo F. J. Org. Chem. 65 (2000) 8340
38. Rajanbabu T.V., Radetich B., You K.K., Ayers T.A., Casalnuovo A.L., and Calabrese J.C. J. Org. Chem. 64 (1999) 3429
39. Busacca C.A., Grossbach D., So R.C., O'Brien E.M., and Spinelli E.M. Org. Lett. 5 (2003) 595
40. Chen Y.-J., Lin R.-X., and Chen C. Tetrahedron: Asymmetry 15 (2004) 3561
41. Lee P.-T., and Chen C. Tetrahedron: Asymmetry 16 (2005) 2704
42. Nettekoven U., Widhalm M., Kalchauser H., Kamer P.C.J., Van Leeuwen P.W.N., Lutz M., and Spek A.L. J. Org. Chem. 66 (2001) 759
43. Alame M., Jahjah M., Pellet-Rostaing S., Lemaire M., Meille V., and De Bellefon C. J. Mol. Catal. A: Chem. 271 (2007) 18
44. Goto, M.; Mano, M. (Takeda Chemical Industries), PCT Int. Appl., WO 03048174, 2003.
45. Goto, M.; Mano, M. (Takeda Chemical Industries), European Patent Appl., EP 1452537, 2004.
46. Uozumi Y., Tanahashi A., Lee S.Y., and Hayashi T. J. Org. Chem. 58 (1993) 1945
47. Mezzetti A., and Consiglio G. J. Chem. Soc., Chem. Commun. (1991) 1675
48. Genêt J.P., Pinel C., Ratovelomanana-Vidal V., Mallart S., Pfister X., Biscoff L., Cano De Andrade M.C., Darses S., Galopin C., and Laffitte J.A. Tetrahedron: Asymmetry 5 (1994) 675
49. Mashima K., Kusano K., Sato N., Matsumura Y., Nozaki K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., and Takaya H. J. Org. Chem. 59 (1994) 3064
50. Sogah G.D.Y., and Cram D.J. J. Am. Chem. Soc. 101 (1979) 3035
51. Hamade T., Fukuda T., Imanishi H., and Katsuki T. Tetrahedron 52 (1996) 515
52. Brisdon B.J., England R., Reza K., and Sainsbury M. Tetrahedron 49 (1993) 1103
53. Olah G.A., Narang S.C., Gupta B.G.B., and Malhotra R. J. Org. Chem. 44 (1979) 1247
54. Uozumi Y., Tanahashi A., Lee S.Y., and Hayashi T. J. Org. Chem. 58 (1993) 1945