Asymmetric hydrogenation - Influence of the structure of carbohydrate derived catalysts on the relative enantioselectivity Q(H/Me) regarding acid and ester substrates and its inversion - Selectivity increase in water by amphiphiles

Tetrahedron

Volumn 52, Issue 48, 1996, Pages 15079-15102

  Selke, Rüdiger ^a   Ohff, Manuela ^a   Riepe, Andreas ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CINNAMIC ACID DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CHELATION; CHIRALITY; DRUG SYNTHESIS; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030602255     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00953-2     Document Type: Article

References (46)

1. 1 Part of the Ph. D. Thesis of Manuela Schwarze, (1995) University Rostock, (now Manuela Ohff by marriage).
2. 2 (a) Selke, R.; Schwarze, M.; Baudisch, H.; Grassert, I.; Michalik, M.; Oehme, G.; Stoll, N.; Costisella, B. J. Mol. Catal. 1993, 84, 223;
3. (b) Casalnuovo, A. L.; RajanBabu, T.V.; Ayers, T. V.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869; and references cited therein.
4. 3 (a) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635;
5. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29;
6. (c) Selke, R. React. Kinet. Catal. Lett. 1979, 10, 135;
7. (d) Selke, R. J. Prakt. Chem. 1987, 329, 717;
8. (e) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101 and references cited therein.
9. 4 (a) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213;
10. (b) Vocke, W.; Hänel, R.; Flöther, F.-U. Chem. Tech. (Leipzig) 1987, 39, 123.
11. 5 (a) Selke, R. J. Organomet. Chem. 1989, 370, 241;
12. (b) Selke, R. J. Organomet. Chem. 1989, 370, 249.
13. 6 (a) Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem. 1994, 106, 2272; Angew. Chem. Int. Ed. Engl. 1994, 33, 2197;
14. 6 (a) Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem. 1994, 106, 2272; Angew. Chem. Int. Ed. Engl. 1994, 33, 2197;
15. (b) Oehme, G.; Paetzold, E.; Selke, R. J. Mol. Catal. 1992, 71, L1.
16. (a) Oehme, G.; Grassert, I.; Flach, N. in Aqueous Organometallic Chemistry and Catalysis Horváth, I. T. and Joo, F. (eds.); Exxon Research and Engineering Company, the Netherlands 1995, 245-257;
17. (b) Flach, H. N.; Grassert, I.; Oehme, G. Macromol. Chem. Phys. 1994, 195, 3289;
18. (c) Grassert, I.; Paetzold, E.; Oehme, G. Tetrahedron 1993, 49, 6605.
19. 8 Patroni, J. J.; Strick, R. V.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1988, 41, 91.
20. I ,-conformation of the hexopyranosides which seems to be valid at least in the ground state of all precatalysts according to NMR measurements; see: Michalik, M.; Freier, T.; Schwarze, M.; Selke, R. Magn. Reson. Chem. 1995, 33, 835.
21. 6a
22. 11 Selke, R.; Ohff, M.; Michalik, M.; Schareina, T.; Heller, D. unpublished results.
23. 12 (a) Knowles, W. S.; Vineyard, B. D.; Sabacky, M. J.; Stults, B. R. Fundamental Research in Homogeneous Catalysis, Tsutsui, M. (Ed.) 1979, 537-547,
24. (b) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.
25. 13 Pavlov, V. A.; Klabunovskii, E. I.; Struchkov, Yu. T.; Voloboev, A. A.; Yanovsky, A. I. J. Mol. Catal. 1988, 44, 217.
26. 14 (a) Seebach, D.; Plattner, D. A.; Beck, A. K..; Wang, J. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171,
27. (b) Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kühnle, F. N. M.; Schweizer, W. B.; Weber, B. Helv. Chim. Acta 1995, 78, 1636.
28. 15 Kempe, R.; Schwarze, M.; Selke, R. Z. Kristallogr. 1995, 210, 155.
29. 16 Selke, R.; Facklam, C.; Foken, H.; Heller, D. Tetrahedron: Asymmetry 1993, 4, 369.
30. 17 Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363, Seebach applied "er" as an abbreviation for the enantiomeric ratio.
31. 18 Kagan, H. B. Recl. Trav. Chim. Pays-Bas 1995, 114, 203.
32. 19 Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055.
33. 20 Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973, Diop stands for 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane.
34. 21 Grassert, I.; Paetzold, E.; Oehme, G. Tetrahedron 1993, 49, 6605. BPPM stands for (2S,45)-4-diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine.
35. 22 (a) Moroi, J. Micelles, Theoretical and Applied Aspects, Plenum Press, New York 1992, 148,
36. (b) Fendler, J. H. Membrane Mimetic Chemistry, Wiley-Interscience, New York 1982, 10.
37. 23 For recent results about aqua complexes of rhodium(I) see Kölle, U.; Görissen, R.; Wagner, T. Chem. Ber. 1995, 128, 911.
38. 24 J. M. Buriak, J. A. Osborn Organometallics 1996, 15, 3161.
39. 25 Os, N. M. van; Haak, J. R.; Rupert, L. A. M. (Eds.) Physico-Chemical Properties of Selected Anionic, Cationic and Nonionic Surfactants, Elsevier, Amsterdam 1993.
40. 26 Becker, H. G. O. et al. Organikum, Barth, Dt. Verl. der Wiss., Leipzig 1993, 667.
41. 27 Freudenberg, K.; Toepffer, A.; Andersen, C. C. Ber. Dtsch. Chem. Ges. 1928, 61, 1750.
42. 28 Most of the 4,6-O-arylidene protected glycopyranosides are known from the literature, reviews see: De Belder, A. N. Adv. Carbohydr. Chem. 1965, 20, 219;
43. De Belder, A. N. Adv. Carbohydr. Chem. Biochem. 1977, 34, 179. Three methyl p-anisylidene glycopyranosides are known, see:
44. Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans 1, 1984, 2371;
45. Classon, B.; Liu, Z. J. Org. Chem. 1988, 53, 6126. All p-anisylidene protected phenyl glycosides are new species.
46. 29 Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213.