Amphiphilic proline and prolylproline derivatives in the rhodium(I)- catalyzed asymmetric hydrogenation in water: Chiral induction as indication of the location of reactants within the micelle

Chirality

Volumn 10, Issue 8, 1998, Pages 754-759

  Grassert, Ingrid ^a   Schinkowski, Klaus ^a   Vollhardt, Dieter ^b   Oehme, Günther ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES   (Germany)

Author keywords

Chiral induction; Critical micellar concentration; Enhanced enantioselectivity; Function of proline; Reaction place; Solubilization

Indexed keywords

AMINO ACID DERIVATIVE; CINNAMIC ACID DERIVATIVE; PROLINE DERIVATIVE; RHODIUM; SURFACTANT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; MICELLE; PRIORITY JOURNAL; SOLUBILIZATION; SURFACE TENSION;

EID: 0031738799     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1998)10:8<754::AID-CHIR6>3.0.CO;2-8     Document Type: Article

References (26)

1. Kunitake, T., Shinkai, S. Catalysis by micelles, membranes and other aqueous aggregates as models of enzyme action. Adv. Phys. Org. Chem. 17:435-487, 1980.
2. Bunton, C.A., Savelli, G. Organic reactivity in aqueous micelles and similar assemblies. Adv. Phys. Org. Chem. 22:213-309, 1986.
3. Oehme, G., Paetzold, E., Selke, R. Increase in activity and enantioselectivity in asymmetric hydrogenation reactions catalyzed by chiral rhodium(I) complexes as a consequence of the action of amphiphiles. J. Mol. Catal. 71:L1-L5, 1992.
4. Grassert, I., Paetzold, E., Oehme, G. Influence of different types of amphiphiles on the rhodium(I) complex-catalyzed asymmetric hydrogenation of (Z)-methyl α-acetamido-cinnamate in aqueous medium. Tetrahedron 49:6605-6612, 1993.
5. Zhang, Y., Bao, W., Dong, H. The asymmetric solvomercuration-demercuration of olefins in chiral micellar systems. Synth. Commun. 23:3029-3035, 1993.
6. 2-induced asymmetric reduction of benzil in the presence of chiral surfactant. Synth. Commun. 24:2437-2440, 1994.
7. Rose, P.L., Harvey, N.G., Arnett, E.M. Chirality and molecular recognition in monolayers at the air-water interface. Adv. Phys. Org. Chem. 28:45-138, 1993.
8. Vollhardt, D. Morphology and phase behaviour of monolayers. Adv. Colloid Interface Sci. 64:143-171, 1996.
9. Dole, M. Surface tension measurements. In Berl, W.G. (ed.): Physical Methods in Chemical Analysis, Vol. II. New York: Academic Press, 1951:305-332.
10. Macy, R. Surface tension by the ring method. Applicability of the Du Noüy apparatus. J. Chem. Educ. 12:573-576, 1935.
11. Huh, C., Mason, S.G. Rigorous theory of ring tensiometry. Colloid Polymer Sci. 253:566-580, 1975.
12. Czichocki, G., Vollhardt, D., Seibt, H. Production and characterization of surface-active chemically pure sodium dodecyl sulfate. Tenside Deterg. 18:320-327, 1981.
13. Grenn, M., Kuc, T.A., Taylor, S.H. Cationic transition-metal complexes, Part I. Synthesis and reactions of bis(diene)-rhodium and -iridium tetrafluoroborates. J. Chem. Soc. (A) 1971:2334-2337.
14. Brown, J.M., Chaloner, P.A., Kent, A.G., Murrer, B.A., Nicholson, P.N., Sidebottom, P.J. The mechanism of asymmetric homogeneous hydrogenation. Solvent complexes and dihydrides from rhodium diphosphine precursors. J. Organomet. Chem. 210:263-276, 1981.
15. Cook, A.H., Harris, G., Heilbron, J. Studies in the azole series, Part V. A synthesis of β-phenylcysteine. J. Chem. Soc. 1948:1060-1065.
16. Brenner, M., Müller, H.R., Pfister, R.W. Eine neue enzymatische Peptidsynthese. Helv. Chim. Acta 33:568-591, 1950.
17. Zeelen, F.J., Havinga, E. Synthesis of stearoylamino acids. Recl. Trav. Chim. Pays-Bas 77:267-272, 1958.
18. Shinitzky, M., Haimovitz, R. Chiral surfaces in micelles of enantiomeric N-palmitoyl- and N-stearoylserine. J. Am. Chem. Soc. 115:12545-12549, 1993.
19. Vaughan, J.R., Jr., Osato, R.L. The preparation of peptides using mixed carbonic-carboxylic acid anhydrides. J. Am. Chem. Soc. 74:676-678, 1952.
20. Iyer, V.N., Subrahmanyam, V.V.R. Effect of structure on surfactants of sodium salts of N-acylamino acids in aqueous solutions. J. Indian Chem. Soc. LXII:507-512, 1985.
21. Desai, A., Singh, J., Kothwala, P.H., Bahadur, P. Surfactant properties of sodium salts of N-acylamino acids. In Mittal, L.L. (ed.): Surfactants in Solution, Vol. 8. New York: Plenum Press, 1989:319-331.
22. Broxton, T.J., Christie, J.R., Dole, A.J. Micellar catalysis of organic reactions. Part 35. Kinetic determination of the critical micelle concentration of cationic micelles in the presence of additives. J. Phys. Org. Chem. 7:437-441, 1994.
23. Rosen, M.J. Surfactants and Interfacial Phenomena, Ed 2. New York: Wiley, 1989:172-174.
24. Fischer, G. Über Peptidyl-Prolyl-cis/trans-Isomerasen und ihre Effektoren. Angew. Chem. 106:1479-1501, 1994.
25. McDonald, Q.D., Still, W.C. Molecular mechanics parameters and conformational free energies of proline-containing peptides. J. Org. Chem. 61:1385-1391, 1996.
26. Beausoleil, E., Lubell, W.D. Steric effects on the amide isomer equilibrium of prolyl peptides. Synthesis and conformational analysis of N-acetyl-5-tert-butylproline N′-methylamides. J. Am. Chem. Soc. 118: 12902-12908, 1996.