Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

Tetrahedron

Volumn 60, Issue 20, 2004, Pages 4399-4412

  Clayden, Jonathan ^a   Lai, Lai Wah ^a   Helliwell, Madeleine ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Atropisomeric amides; Ephedrine; Imidazolines; Oxazolidines

Indexed keywords

AMIDE; EPHEDRINE; IMIDAZOLINE DERIVATIVE; OXAZOLIDINE DERIVATIVE; PROLINE;

ARTICLE; CRYSTAL STRUCTURE; HYDROLYSIS; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 1942436911     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.101     Document Type: Article

References (64)

1. Bowles P., Clayden J., Helliwell M., McCarthy C., Tomkinson M., Westlund N. J. Chem. Soc., Perkin Trans. 1. 1997;2607.
2. Cuyegkeng M.A., Mannschreck A. Chem. Ber. 120:1987;803.
3. Pirkle W.H., Welch C.J., Zych A.J. J. Chromatogr. A. 648:1993;101.
4. Dai W.-M., Yeung K.K.Y., Chow C.W., Williams I.D. Tetrahedron: Asymmetry. 12:2001;1603.
5. Ackerman J.H., Laidlaw G.M., Snyder G.A. Tetrahedron Lett. 1969;3879.
6. Rosini C., Franzini L., Raffaelli A., Salvadori P. Synthesis. 1992;503.
7. Noyori R. Asymmetric catalysis in organic synthesis. 1994;Wiley, New York.
8. Miyashita A., Takaya H., Souchi T., Noyori R. Tetrahedron. 40:1984;1245.
9. Dai W.-M., Yeing K.K.Y., Liu J.-T., Zhang Y., Williams I.D. Org. Lett. 4:2002;1615.
10. Clayden J., Johnson P., Pink J.H., Helliwell M. J. Org. Chem. 65:2000;7033.
11. Clayden J., Lai L.W., Helliwell M. Tetrahedron: Asymmetry. 12:2001;695.
12. Rios R., Kimeno C., Carroll P.J., Walsh P.J. J. Am. Chem. Soc. 124:2002;10272.
13. Dai W.-M., Lau C.-W. Tetrahedron Lett. 2001;2541.
14. Thayumanavan S., Beak P., Curran D.P. Tetrahedron Lett. 37:1996;2899.
15. Koide H., Uemura M. Chem. Commun. 1998;2483.
16. Koide H., Hata T., Uemura M. J. Org. Chem. 67:2002;1929.
17. Clayden J., Johnson P., Pink J.H. J. Chem. Soc., Perkin Trans. 1. 2001;371.
18. Clayden J., McCarthy C., Cumming J.G. Tetrahedron Lett. 41:2000;3279.
19. Ikeura Y., Ishichi Y., Tanaka T., Fujishima A., Murabayashi M., Kawada M., Ishimaru T., Kamo I., Doi T., Natsugari H. J. Med. Chem. 41:1998;4232.
20. Ikeura Y., Ishimaru T., Doi T., Kawada M., Fujishima A., Natsugari H. Chem. Commun. 1998;2141.
21. Mikata Y., Hayashi K., Mizukami K., Matsumoto S., Yano S., Yamazaki N., Ohno A. Tetrahedron Lett. 41:2000;1035.
22. Mikata Y., Mizukami K., Hayashi K., Matsumoto S., Yano S., Yamazaki N., Ohno A. J. Org. Chem. 66:2001;1590.
23. van Lier P.M., Meulendijks G.H.W.M., Buck H.M. Rec. Trav. Chim. Pays-Bas. 102:1983;337.
24. Donkersloot M.C.A., Buck H.M. J. Am. Chem. Soc. 103:1981;6589.
25. Vekemans J.A.J.M., Boogers J.A.F., Buck H.M. J. Org. Chem. 56:1991;10.
26. Preliminary communications: Refs. 27 and 28.
27. Clayden J., Lai L.W. Angew. Chem., Int. Ed. 38:1999;2556.
28. Clayden J., Lai L.W. Tetrahedron Lett. 42:2001;3163.
29. Beak P., Anderson D.R., Curtis M.D., Laumer J.M., Pippel D.J., Weisenburger G.A. Acc. Chem. Res. 33:2000;715.
30. Clayden J., McCarthy C., Westlund N., Frampton C.S. J. Chem. Soc., Perkin Trans. 1. 2000;1363.
31. Clayden J., Frampton C.S., McCarthy C., Westlund N. Tetrahedron. 55:1999;14161.
32. Beak P., Brown R.A. J. Org. Chem. 42:1977;1823.
33. Snieckus V. Chem. Rev. 90:1990;879.
34. Mills R.J., Taylor N.J., Snieckus V. J. Org. Chem. 54:1989;4372.
35. Court J.J., Hlasta D.J. Tetrahedron Lett. 37:1996;1335.
36. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4155.
37. Boeckman R.K., Shao P., Mullins J.J. Org. Synth. 77:2000;141.
38. Alexakis A., Mangeney P., Lensen N., Tranchier J., Gosmini R., Raussou S. Pure Appl. Chem. 68:1996;531.
39. Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869.
40. Iriuchijima S. Synthesis. 1978;684.
41. Mukaiyama T., Sakito Y., Asami M. Chem. Lett. 1978;1253.
42. Meyers A.I., Flisak J.R., Aitken R.A. J. Am. Chem. Soc. 109:1987;5446.
43. Ahmed A., Bragg R.A., Clayden J., Lai L.W., McCarthy C., Pink J.H., Westlund N., Yasin S.A. Tetrahedron. 54:1998;13277.
44. Kamikawa K., Uemura M. Synlett. 2000;938.
45. Clayden J., Helliwell M., McCarthy C., Westlund N. J. Chem. Soc., Perkin Trans. 1. 2000;3232.
46. On a large scale, the method of Iriuchijima (Ref. 40) is preferable, but care must be taken not to racemise the pyroglutamate during anilide formation.
47. Clark R.D., Jahangir A. Org. React. 47:1995;1.
48. Neelakantan L. J. Org. Chem. 36:1971;2256.
49. Santiesteban F., Grimaldo C., Contreras R., Wrackmeyer B. Chem. Commun. 1983;1486.
50. Agami C., Rizk T. Chem. Commun. 1983;1485.
51. Agami C., Rizk T. Tetrahedron. 41:1985;537.
52. 1H NMR of endo ephedrine-derived oxazolidines, see: Clayden, J.; Foricher, Y. J. Y; Johnson, P.; Youssef, L. H. Manuscript in preparation.
53. We have previously reported the hydrolysis of imidazolidines derived from 1c and 1d without racemisation (Refs. 18, 45) - but the Ar-CO axes of these compounds are stabilised by the presence of the peri substituent.
54. Noyori R., Tokunaga M., Kitamura M. Bull. Chem. Soc. Jpn. 68:1995;36.
55. Bringmann G., Hinrichs J., Pabst T., Henschel P., Peters K., Peters E.-M. Synthesis. 2001;155.
56. Caddick S., Jenkins K. Chem. Soc. Rev. 36:1996;1173.
57. Ward R.S. Tetrahedron: Asymmetry. 6:1995;1475.
58. Clayden J., McCarthy C., Helliwell M. Chem. Commun. 1999;2059.
59. Clayden J., Mitjans D., Youssef L.H. J. Am. Chem. Soc. 124:2002;5266.
60. Chen C.-W., Beak P. J. Org. Chem. 51:1986;3325.
61. De Silva S.O., Reed J.N., Billedeau R.J., Wang X., Norris D.J., Snieckus V. Tetrahedron. 48:1992;4863.
62. Still W.C., Kahn M., Mitra A. J. Org. Chem. 43:1978;2923.
63. Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 34:1969;2543.
64. Pirkle W.H., Sikkenga D.L., Pavlin M.S. J. Org. Chem. 42:1977;384.