Polyamino acids as catalysts in asymmetric synthesis

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 10, 1999, Pages 2145-2156

  Porter, Michael J ^a   Roberts, Stanley M ^a   Skidmore, John ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Amino acids and derivatives; Peptides and polypeptides; Polymers; Reviews

Indexed keywords

ALANINE; EPOXIDE; HYDROGEN PEROXIDE; KETONE DERIVATIVE; LEUCINE; POLYAMINOACID;

AMINO ACID SYNTHESIS; BIOSYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; EPOXIDATION; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; REVIEW;

AMINO ACIDS; CATALYSIS; CHEMISTRY, ORGANIC; EPOXY COMPOUNDS; HYDROGEN PEROXIDE; KETONES; PEPTIDES;

EID: 0032874208     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00144-3     Document Type: Review

References (81)

1. Wong C.H., Whitesides G.M. Enzymes in Organic Synthesis. 1994;Pergamon, Oxford.
2. Drauz, K.; Waldmann, H., Eds. Enzyme Catalysts in Organic Synthesis; VCH: Weinheim, 1995.
3. Faber K. Biotransformations in Organic Chemistry. 1996;Springer-Verlag, Berlin.
4. For some recent examples, see Roberts, S. M. J. Chem. Soc., Perkin Trans 1 1998, 157-169.
5. de Raadt A., Griengl H., Petsch M., Plachota P., Schoo N., Weber H., Braunegg G., Kopper I., Kreiner M., Zeiser A., Kieslich K. Tetrahedron. Asymmetry 7:1996;467-472.
6. de Raadt A., Griengl H., Petsch M., Plachota P., Schoo N., Weber H., Braunegg G., Kopper I., Kreiner M., Zeiser A. Tetrahedron. Asymmetry 7:1996;473-490.
7. de Raadt A., Griengl H., Petsch M., Plachota P., Schoo N., Weber H., Braunegg G., Kopper I., Kreiner M., Zeiser A. Tetrahedron. Asymmetry 7:1996;491-496.
8. See, for example, Dingler, C.; Ladner, W.; Krei, G. A.; Cooper, B.; Hauer, B. Pesticide Science 1996, 46, 33-35.
9. Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000.
10. Banwell, M.; De Savi, C.; Watson, K. Chem. Commun. 1998, 1189-1190.
11. See, for example, Mahmoudian, M.; Michael, A. Appl. Microbiol. Biotechnol. 1992, 37, 23-27 and ref. 12.
12. Mahmoudian, M.; Michael, A. Appl. Microbiol. Biotechnol. 1992, 37, 28-31.
13. Juliá S., Masana J., Vega J.C. Angew. Chem. Int. Ed. Engl. 19:1980;929-931.
14. For recent complementary reviews on this subject, see Ebrahim, S.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 3163-3173 and ref. 15.
15. Pu L. Tetrahedron. Asymmetry 9:1998;1457-1477.
16. For other recently reported methods for asymmetric epoxidation of enones, see Baccin, C.; Gusso, A.; Pinna, F.; Strukul, G. Organometallics 1995, 14, 1161-1167 and refs. 17-21.
17. Bougauchi M., Watanabe S., Arai T., Sasai H., Shibasaki M. J. Am. Chem. Soc. 119:1997;2329-2330.
18. Elston C.L., Jackson R.F.W., MacDonald S.J.F., Murray P.J. Angew. Chem. Int. Ed. Engl. 36:1997;410-412.
19. Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Receuil 1997, 1101-1113.
20. Wang Z.-X., Shi Y. J. Org. Chem. 62:1997;8622-8623.
21. Lygo B., Wainwright P.G. Tetrahedron Lett. 39:1998;1599-1602.
22. Fuchs F. Ber. 55:1922;189.
23. Baird, W.; Parry, E. G.; Robinson, S. Brit. Patent 646033, 1950.
24. Oya, M.; Katakai, R.; Nakai, H.; Iwakura, Y. Chem. Lett. 1973, 1143-1144.
25. Katakai R., Iizuka Y. J. Org. Chem. 50:1985;715-716.
26. Daly W.H., Poche D. Tetrahedron Lett. 29:1988;5859-5862.
27. Leuchs H. Ber. 39:1906;857-861.
28. Leuchs H., Geiger W. Ber. 41:1908;1721-1726.
29. Woodward R.B., Schramm C.H. J. Am. Chem. Soc. 69:1947;1551-1552.
30. Coleman, D. J. Chem. Soc. 1950, 3222-3229.
31. Lasterra-Sánchez, M. E.; Felfer, U.; Mayon, P.; Roberts, S. M.; Thornton, S. R.; Todd, C. J. J. Chem. Soc., Perkin Trans. 1 1996, 343-348.
32. For reviews on polymerisation of NCAs, see Sekiguchi, H. Pure Appl. Chem. 1981, 53, 1689-1714 and ref. 33.
33. Kricheldorf, H. R. In Comprehensive Polymer Science; Allen, G.; Bevington, J. C., Eds.; Pergamon: Oxford, 1989; Vol. 3, pp 531-551.
34. Banfi S., Colonna S., Molinari H., Julia S., Guixer J. Tetrahedron. 40:1984;5207-5211.
35. Itsuno S., Sakakura M., Ito K. J. Org. Chem. 55:1990;6047-6049.
36. Cappi, M. W.; Chen, W.-P.; Flood, R. W.; Liao, Y.-W.; Roberts, S. M.; Skidmore, J.; Smith, J. A.; Williamson, N. M. Chem. Commun. 1998, 1159-1160.
37. Hirayama C., Ihara H., Tanaka K. J. Chromat. 450:1988;271-276.
38. Sinibaldi M., Catellani L., Federici F., Messina A. J. Liq. Chromat. 16:1993;2977-2992.
39. Shyu S.S., Kuroyanagi Y., Seno M. Colloid Polym. Sci. 266:1988;587-593.
40. Kuroyanagi Y., Kim E., Kenmochi M., Ui K., Kageyama H., Nakamura M., Takeda A., Shioya N. J. Appl. Biomater. 3:1992;153-161.
41. Akabori S., Sakurai S., Izumi Y., Fujii Y. Nature. 178:1956;323-324.
42. Alper, H., Hamel, N. J. Chem. Soc., Chem. Commun. 1990, 135-136.
43. Abe S., Nonaka T., Fuchigami T. J. Am. Chem. Soc. 105:1983;3630-3632.
44. Nonaka T., Abe S., Fuchigami T. Bull. Chem. Soc. Jpn. 56:1983;2778-2783.
45. Abe, S.; Nonaka, T. Chem. Lett. 1983, 1541-1542.
46. Abe, S.; Fuchigami, T.; Nonaka, T. Chem. Lett. 1983, 1033-1036.
47. Komori, T.; Nonaka, T. J. Am. Chem. Soc. 1983, 105, 5690-5691.
48. Komori T., Nonaka T. J. Am. Chem. Soc. 106:1984;2656-2659.
49. Juliá, S.; Guixer, J.; Masana, J.; Rocas, J.; Colonna, S.; Annuziata, R.; Molinari, H. J. Chem. Soc., Perkin Trans. 1 1982, 1317-1324.
50. Julia S., Masana J., Rocas J., Colonna S., Annunziata R., Molinari H. Anal. Quim. 79:1983;102-104.
51. Colonna S., Molinari H., Banfi S., Juliá S., Masana J., Alvarez A. Tetrahedron. 39:1983;1635-1641.
52. Flisak J.R., Gombatz K.J., Holmes M.M., Jarmas A.A., Lantos I., Mendelson W.L., Novack V.J., Remich J.J., Snyder L. J. Org. Chem. 58:1993;6247-6254.
53. As the catalysts are prepared by an uncontrolled polymerisation reaction they are not homogeneous, instead a statistical distribution of chain lengths is present, dependent on the ratio of initiator to NCA employed in the polymerisation procedure. It is common in the literature for a polymer to be referred to as being of length n, where n is in fact the mean length.
54. Bezuidenhoudt B.C.B., Swanepoel A., Augustyn J.A.N., Ferreira D. Tetrahedron Lett. 28:1987;4857-4860.
55. Augustyn J.A.N., Bezuidenhoudt B.C.B., Ferreira D. Tetrahedron. 46:1990;2651-2660.
56. Augustyn J.A.N., Bezuidenhoudt B.C.B., Swanepoel A., Ferreira D. Tetrahedron. 46:1990;4429-4442.
57. van Rensburg, H.; van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Chem. Commun. 1996, 2747-2748.
58. van Rensburg H., van Heerden P.S., Bezuidenhoudt B.C.B., Ferreira D. Tetrahedron. 53:1997;14141-14152.
59. Lasterra-Sánchez M.E., Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 1:1995;1467-1468.
60. Kroutil, W.; Mayon, P.; Lasterra-Sánchez, M. E.; Maddrell, S. J.; Roberts, S. M.; Thornton, S. R.; Todd, C. J.; Tüter, M. Chem. Commun. 1996, 845-846.
61. Kroutil; W.; Mayon; P.; Lasterra-Sánchez; M. E.; Maddrell; S. J.; Roberts; S. M.; Thornton; S. R.; Todd; C. J.; Tüter, M. Chem. Commun. 1996, 2495.
62. Kroutil W., Lasterra-Sánchez M.E., Maddrell S.J., Mayon P., Morgan P., Roberts S.M., Thornton S.R., Todd C.J., Tüter M. J. Chem. Soc., Perkin Trans. 1. 1:1996;2837-2844.
63. Falck; J. R.; Bhatt; R. K.; Reddy; K. M.; Ye; J. H. Synlett 1997, 481-482.
64. Bentley, P. A.; Bergeron; S.; Cappi; M. W.; Hibbs; D. E.; Hursthouse; M. B.; Nugent; T. C.; Pulido; R.; Roberts; S. M.; Wu, L. E. Chem. Commun. 1997, 739-740.
65. Cooper; M. S.; Heaney; H.; Newbold; A. J.; Sanderson; W. R. Synlett 1990, 533-535.
66. Oswald A.A., Guertin D.L. J. Org. Chem. 28:1963;651-657.
67. Allen J.V., Cappi M.W., Kary P.D., Roberts S.M., Williamson N.M., Wu L.E. J. Chem. Soc., Perkin Trans. 1. 1:1997;3297-3298.
68. Adger B.M., Barkley J.V., Bergeron S., Cappi M.W., Flowerdew B.E., Jackson M.P., McCague R., Nugent T.C., Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 1:1997;3501-3507.
69. Mukherjee, S., Roberts, S. M., unpublished results.
70. Chen W.-P., Egar A.L., Hursthouse M.B., Abdul Malik K.M., Mathews J.E., Roberts S.M. Tetrahedron Lett. 39:1998;8495-8498.
71. Bentley, P. A., Roberts, S. M., unpublished results.
72. Allen J.V., Bergeron S., Griffiths M.J., Mukherjee S., Roberts S.M., Williamson N.M., Wu L.E. J. Chem. Soc., Perkin Trans. 1. 1:1998;3171-3179.
73. Baures P.W., Eggleston D.S., Flisak J.R., Gombatz K., Lantos I., Mendelson W., Remich J.J. Tetrahedron Lett. 31:1990;6501-6504.
74. Gillmore A.T., Roberts S.M., Hursthouse M.B., Abdul Malik K.M. Tetrahedron Lett. 39:1998;3315-3318.
75. Carde; L.; Davies; H.; Pulido; R.; Roberts; S. M., unpublished results.
76. Banfi S., Colonna S., Molinari H., Julia S. Synth. Commun. 13:1983;901-904.
77. Hashiyama T., Inoue H., Konda M., Takeda M. J. Chem. Soc., Perkin Trans. 1. 1:1984;1725-1732.
78. Schwartz A., Madan P.B., Mohacsi E., O'Brien J.P., Todaro L.J., Coffen D.L. J. Org. Chem. 57:1992;851-856.
79. For studies on the physical properties of the polyamino acid catalyst, see Valencia-Parera, G.; Solans-Marsa, C.; Reig-Isart, F.; Garcia-Anton, J. M. J. Colloid Interf. Sci. 1986, 114, 140-148 and ref. 80.
80. Bentley P.A., Kroutil W., Littlechild J.A., Roberts S.M. Chirality. 9:1997;198-202.
81. Available from UFC-Pharma, Science Park, Manchester, M15 6SY, UK.