2,2′-Bis-[bis(4-substituted-phenyl)phosphino]-1,1′-binaphthyl derivatives in Rh(I)-catalyzed hydrogenation of acetamidoacrylic acid derivatives: Electronic effects

Journal of Molecular Catalysis A: Chemical

Volumn 271, Issue 1-2, 2007, Pages 18-24

  Alame M ^a   Jahjah, M ^a   Pellet Rostaing, S ^a   Lemaire, M ^a   Meille, V ^a   de Bellefon, C ^a  

^a CPE LYON   (France)

Author keywords

BINAP; Electronic effect; Enantioselectivity; Hydrogenation; Rhodium

Indexed keywords

CATALYSIS; ELECTRONS; ENANTIOMERS; ENANTIOSELECTIVITY; HYDROGENATION; LIGANDS; RHODIUM COMPOUNDS;

ACETAMIDOACRYLIC ACID; ELECTRONIC EFFECTS; HAMMETT COEFFICIENTS; PHENYL MOIETIES;

ORGANIC COMPOUNDS;

EID: 34248182943     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2007.02.027     Document Type: Article

References (42)

1. Brunner H., and Zettlmeiner W. Handbook of Enantioselective Catalysis with Transition Metal Compounds Ligands vol. 2 (1993), VCH, Weinheim
2. Seyden-Penne J. Chiral Auxiliairies and Ligands in Asymmetric Synthesis; (1995), John Wiley and Sons, New York pp. 367 (Chapter 7)
3. Mignani G., Woodward G., and Lemaire M. Chem. Rev. 105 (2005) 1801 (For recent review, see M. Berthod)
4. Schmid R., Cereghetti M., Heiser B., Schönholzer P., and Hansen H.-J. Helv. Chim. Acta 71 (1988) 897
5. Schmid R., Foricher J., Cereghetti M., and Schönholzer P. Helv. Chim. Acta 74 (1991) 370
6. Schmid R., Broger E.A., Cereghetti M., Crameri Y., Foricher J., Lalonde M., Müller R.K., Scalone M., Schottel G., and Zutter U. Pure Appl. Chem. 68 (1996) 131
7. Duprat de Paul S., Jeulin S., Ratovelomanana-Vidal V., Genêt J.-P., Champion N., and Dellis P. Tetrahedron Lett. 44 (2003) 823
8. Duprat de Paul S., Jeulin S., Ratovelomanana-Vidal V., Genêt J.-P., Champion N., and Dellis P. Org. Process Res. Dev. 7 (2003) 399
9. Saito T., Yokozawa T., Ishizaki T., Moroi T., Sayo N., Miura T., and Kumobayashi H. Adv. Synth. Catal. 343 (2001) 264
10. Noyori R., and Takaya H. Acc. Chem. Res. 23 (1990) 345
11. Takaya H., Otha T., and Noyori R. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis (1993), VCH, New York
12. Duprat de Paule S., Jeulin S., Ratovelomanana-Vidal V., Genêt J.P., Champion N., Deschaux G., and Dellis P. Org. Process Res. Dev. 7 (2003) 399
13. Hopkins J.M., Dalrymple S.A., Parvez M., and Keay B.A. Org. Lett. 7 (2005) 3765
14. Hu A., Ngo H.L., and Lin W. Angew. Chem. Int. Ed. 43 (2004) 2501
15. Alame M., Jahja M., Berthod M., Lemaire M., Meille V., and de Bellefon C. J. Mol. Catal. A 268 (2007) 205
16. Kumobayashi H., Miura T., Sayo N., Saito T., and Zhang X. Synlett (2001) 1055
17. Duprat de Paule S., Jeulin S., Ratovelomanana-Vidal V., Genêt J.P., Champion N., Deschaux G., and Dellis P. Tetrahedron Lett. 44 (2003) 823
18. Allen D.W., and Taylor B.F. J. Chem. Soc. Dalton Trans. (1982) 51
19. Mashima K., Kusano K.-H., Sato N., Matsumura Y.-I., Nozaki K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., and Takaya H. J. Org. Chem. 59 (1994) 3064
20. 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
21. Murata M., Morimoto T., and Achiwa K. Synlett (1991) 827
22. Benincori T., Piccolo O., Rizzo S., and Sannicolo F. J. Org. Chem. 65 (2000) 8340
23. Jeulin S., Duprat de Paule S., Ratovelomanana-Vidal V., Genêt J.P., Champion N., and Dellis P. Angew. Chem. Int. Ed. 43 (2004) 320
24. Miyashita A., Yasuda A., Takaya H., Toriumi K., Ito T., Souchi T., and Noyori R. J. Am. Chem. Soc. 102 (1980) 7932
25. Miyashita A., Takaya H., Souchi T., and Noyori R. Tetrahedron 40 40 (1984) 1245
26. Jacobsen E.N., Zhang W., and Güler M.L. J. Am. Chem. Soc. 113 113 (1991) 6703
27. Cavallo L., and Jacobsen H. J. Org. Chem. 68 (2003) 6202
28. Rajanbabu T.V., Radetich B., You K.K., Ayers T.A., Casalnuovo A.L., and Calabrese J.C. J. Org. Chem. 64 (1999) 3429
29. 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
30. Palucki M., Finney N.S., Pospisil P.J., Güler M.L., Ishida T., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 948
31. Nakagawa H., Sei Y., Yamaguchi K., Nagano T., and Higuchi T. Tetrahedron: Asymmetry 15 (2004) 3861
32. Park S.-B., Murata K., Matsumoto H., and Nishiyama H. Tetrahedron: Asymmetry 6 (1995) 2487
33. Busacca C.A., Grossbach D., So R.C., O'Brien E.M., and Spinelli E.M. Org. Lett. 5 (2003) 595
34. Uozumi Y., Tamahashi A., Lee S.Y., and Hayashi T. J. Org. Chem. 58 (1993) 1945
35. Stankevic M., and Pietrusiewicz K.M. Synlett 7 (2003) 1012
36. Bayardon J., Cavazzini M., Maillard D., Pozzi G., Quici S., and Sinou D. Tetrahedron: Asymmetry 14 (2003) 2215-2224
37. G. Mitsutaka, Y. Mitsuhisa, WO 2003048174, 12-06-2003.
38. Busacca C.A., Lorenz J.C., Grinberg N., Haddad N., Hrapchak M., Latli B., Lee H., Sabila P., Saha A., Sarvestani M., Shen S., Varsolona R., Wie X., and Senanayake C.H. Org. Lett. 7 (2005) 4277
39. Smith M.B., and March J. March's Advanced Organic Chemistry. fifth ed. 363 (2001) (Chapter 9)
40. Matsui T., Ko H.C., and Hepler L.G. Can. J. Chem. 52 (1974) 2906
41. McDaniel D.H., and Brown H.C. J. Org. Chem. 23 23 (1958) 420
42. Hammett L.P. Physical Organic Chemistry. second ed. (1970), McGraw-Hill, New York