Asymmetric hydrogenation of enamides in aqueous media with a new water-soluble chiral rhodium-α,α-trehalose-derived phosphine-phosphinite catalyst

Tetrahedron Asymmetry

Volumn 13, Issue 19, 2002, Pages 2155-2160

  Ohe, Kouichi ^a   Morioka, Kiyoharu ^a   Yonehara, Koji ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; LIGAND; PHOSPHINE; PHOSPHINIC ACID DERIVATIVE; RHODIUM; TREHALOSE; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; GAS LIQUID CHROMATOGRAPHY; HYDROGENATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; THIN LAYER CHROMATOGRAPHY;

EID: 0037020345     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00569-4     Document Type: Article

References (36)

1. For reviews, see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994; (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, Chapter 5.1; (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: Weinheim, 2000; Chapter 1.3.
2. For reviews, see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994; (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, Chapter 5.1; (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: Weinheim, 2000; Chapter 1.3.
3. For reviews, see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994; (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, Chapter 5.1; (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: Weinheim, 2000; Chapter 1.3.
4. Pamiez O., Diéguez M., Net G., Ruiz A., Claver C. J. Org. Chem. 66:2001;8364.
5. Deerenburg S., Pamiez O., Diéguez M., Claver C., Kamer P.C.J., van Leeuwen P.W.N.M. J. Org. Chem. 66:2001;7626.
6. Pamiez O., Diéguez M., Net G., Ritz A., Claver C. Chem. Commun. 2000;2383.
7. (a) Monsees, A.; Laschat, S. Synlett 2002, 1011;
8. (b) Nozaki, K.; Li, W.; Horiuchi, T.; Takaya, H.; Saito, T.; Yoshida, A.; Matsumura, K.; Kato, Y.; Imai, T.; Miura, T.; Kumobayashi, H. J. Org. Chem. 1996, 61, 7658;
9. (c) Brunner, H.; Pieronczyk, J. J. Chem. Res. Synop. 1980, 76.
10. For aminophosphine-phosphinite ligands, see: (d) Li, X.; Lou, R.; Yeung, C.-H.; Chan, A. S. C.; Wong, W. K. Tetrahedron: Asymmetry 2000, 11, 2077; (e) Xie, Y.; Lou, R.; Li, Z.; Mi, A.; Jiang, Y. Tetrahedron: Asymmetry 2000, 11, 1487; (f) Mi, A.; Lou, R.; Jiang, Y.; Deng, J.; Qin, Y.; Fu, F.; Li, Z.; Hu, W.; Chan, A. S. C. Synlett 1998, 847; (g) Agbossou, F.; Carpentier, J.-F.; Hapiot, F.; Suisse, I.; Mortreux, A. Coord. Chem. Rev. 1998, 178-180, 1615.
11. For aminophosphine-phosphinite ligands, see: (d) Li, X.; Lou, R.; Yeung, C.-H.; Chan, A. S. C.; Wong, W. K. Tetrahedron: Asymmetry 2000, 11, 2077; (e) Xie, Y.; Lou, R.; Li, Z.; Mi, A.; Jiang, Y. Tetrahedron: Asymmetry 2000, 11, 1487; (f) Mi, A.; Lou, R.; Jiang, Y.; Deng, J.; Qin, Y.; Fu, F.; Li, Z.; Hu, W.; Chan, A. S. C. Synlett 1998, 847; (g) Agbossou, F.; Carpentier, J.-F.; Hapiot, F.; Suisse, I.; Mortreux, A. Coord. Chem. Rev. 1998, 178-180, 1615.
12. For aminophosphine-phosphinite ligands, see: (d) Li, X.; Lou, R.; Yeung, C.-H.; Chan, A. S. C.; Wong, W. K. Tetrahedron: Asymmetry 2000, 11, 2077; (e) Xie, Y.; Lou, R.; Li, Z.; Mi, A.; Jiang, Y. Tetrahedron: Asymmetry 2000, 11, 1487; (f) Mi, A.; Lou, R.; Jiang, Y.; Deng, J.; Qin, Y.; Fu, F.; Li, Z.; Hu, W.; Chan, A. S. C. Synlett 1998, 847; (g) Agbossou, F.; Carpentier, J.-F.; Hapiot, F.; Suisse, I.; Mortreux, A. Coord. Chem. Rev. 1998, 178-180, 1615.
13. For aminophosphine-phosphinite ligands, see: (d) Li, X.; Lou, R.; Yeung, C.-H.; Chan, A. S. C.; Wong, W. K. Tetrahedron: Asymmetry 2000, 11, 2077; (e) Xie, Y.; Lou, R.; Li, Z.; Mi, A.; Jiang, Y. Tetrahedron: Asymmetry 2000, 11, 1487; (f) Mi, A.; Lou, R.; Jiang, Y.; Deng, J.; Qin, Y.; Fu, F.; Li, Z.; Hu, W.; Chan, A. S. C. Synlett 1998, 847; (g) Agbossou, F.; Carpentier, J.-F.; Hapiot, F.; Suisse, I.; Mortreux, A. Coord. Chem. Rev. 1998, 178-180, 1615.
14. Ohe K., Yonehara K., Uemura S. J. Synth. Org. Chem. Jpn. 59:2001;185.
15. Steiborn D., Junicke H. Chem. Rev. 100:2000;4283.
16. RajanBabu T.V., Casalnuovo A.L., Ayers T.A. Doyle M.P., Advances in Catalytic Processes. 2:1998;1 JAI Press, Greenwhich.
17. For recent advances in this area, see: (a) Diéguez, M.; Ruiz, A.; Claver, C. J. Org. Chem. 2002, 67, 3796; (b) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734; (c) RajanBabu, T. V.; Yan, Y.-Y.; Shin, S. J. Am. Chem. Soc. 2001, 123, 10207; (d) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489; (e) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229.
18. For recent advances in this area, see: (a) Diéguez, M.; Ruiz, A.; Claver, C. J. Org. Chem. 2002, 67, 3796; (b) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734; (c) RajanBabu, T. V.; Yan, Y.-Y.; Shin, S. J. Am. Chem. Soc. 2001, 123, 10207; (d) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489; (e) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229.
19. For recent advances in this area, see: (a) Diéguez, M.; Ruiz, A.; Claver, C. J. Org. Chem. 2002, 67, 3796; (b) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734; (c) RajanBabu, T. V.; Yan, Y.-Y.; Shin, S. J. Am. Chem. Soc. 2001, 123, 10207; (d) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489; (e) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229.
20. For recent advances in this area, see: (a) Diéguez, M.; Ruiz, A.; Claver, C. J. Org. Chem. 2002, 67, 3796; (b) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734; (c) RajanBabu, T. V.; Yan, Y.-Y.; Shin, S. J. Am. Chem. Soc. 2001, 123, 10207; (d) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489; (e) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229.
21. For recent advances in this area, see: (a) Diéguez, M.; Ruiz, A.; Claver, C. J. Org. Chem. 2002, 67, 3796; (b) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734; (c) RajanBabu, T. V.; Yan, Y.-Y.; Shin, S. J. Am. Chem. Soc. 2001, 123, 10207; (d) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489; (e) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229.
22. Yonehara K., Hashizume T., Mori K., Ohe K., Uemura S. J. Org. Chem. 64:1999;5593.
23. Yonehara K., Ohe K., Uemura S. J. Org. Chem. 64:1999;9381.
24. Hashizume T., Yonehara K., Ohe K., Uemura S. J. Org. Chem. 65:2000;5197.
25. Yonehara K., Hashizume T., Ohe K., Uemura S. Tetrahedron: Asymmetry. 10:1999;4029.
26. Wallace P.A., Minnikin D.E. Carbohydr. Res. 263:1994;43.
27. The use of NaOEt in EtOH-acetone instead of a mixed base resulted in lower yield of 6 along with many by-products.
28. For the related synthesis of 2,3-anhydro-4,6-O-benzylidene-α-D-allopyransyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside, see: Hough L., Munroe P.A., Richardson A.C. J. Chem. Soc. (C). 1971;1090.
29. 2 gave methyl 2-deoxy-2-(diphenylphosphino)-4,6-O-benzylidene-α-D-altropyranoside, see: Shi J.-C., Hong M.-C., Wu D.-X., Liu Q.-T., Kang B.-S. Chem. Lett. 1995;685.
30. Selke R. J. Organomet. Chem. 370:1989;241 Ref. 6a .
31. Ref. 1a Pfaltz, A.; Brown, J. M. In Houben-Weyl Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, Germany, 1995; Vol. E21, Section D.2.5.1.2.
32. Zhang X. Enantiomer. 4:1999;541.
33. Recently other groups have reported that both enantioselectivity and activity were enhanced when the hydrogen pressure was raised in rhodium-catalyzed hydrogenations with a monodentate phosphramidite and bidentate diphosphite ligands, see: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539; (b) Ref. 5a.
34. Recently other groups have reported that both enantioselectivity and activity were enhanced when the hydrogen pressure was raised in rhodium-catalyzed hydrogenations with a monodentate phosphramidite and bidentate diphosphite ligands, see: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539; (b) Ref. 5a.
35. The catalyst 8 is insoluble in EtOAc. Catalyst leaching into EtOAc is therefore unlikely (no coloring of the organic phase was visibly observed). It is tempting to speculate that the loss of reactivity and selectivity is related to the decomposition of 8 causing leaching of the ligand portion into the organic phase under the recycling conditions.
36. The ligands 1a and 1b having a (2R,3S)-glucopyranoside backbone provide (S)-α-amino acid derivatives in the asymmetric hydrogenation of enamides, although they form seven-membered complexes with rhodium, see: Ref. 6a .