Syntheses of isotopically labelled L-α-amino acids with an asymmetric centre at C-3

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 20, 2000, Pages 3406-3416

  Harding, John R ^a   Hughes, Rachael A ^b   Kelly, Nicholas M ^a   Sutherland, Andrew ^b   Willis, Christine L ^a  

^a ASTRAZENECA   (United Kingdom)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMES; ESTERS; HYDROPHOBICITY; ISOTOPES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

LACTIC ACID;

AMINO ACIDS;

EID: 0034700026     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/B005172L     Document Type: Article

References (72)

1. D. W. Young, Chem. Soc. Rcv., 1994, 23, 119;
2. M. P. Crump, J. Crosby, C. E. Dempsey, J. A. Parkinson, M. Murray, D. A. Hopwood and T. J. Simpson, Biochemistry, 1997,36, 6000.
3. J. C. Vederas, Nat. Prod. Rep., 1987, 4, 277.
4. For reviews see: F. J. Winkler, K. Kuhnl, R. Medina, R. SchwarzKoske and H. L. Schmidt, Isot. Environ. Health Stud., 1995, 31, 161;
5. N. M. Kelly, A. Sutherland and C. L. Willis, Nat. Prod Rep., 1997,14,205.
6. Y. Yamamoto, W. Ito and K. Maruyama, J. Chem. Soc., Chem. Commun., 1985, 1131.
7. P. Lloyd-Williams, P. Monerris, I. Gonzalez, G. Jou and E. Giralt, J. Chem. Soc., Perkin Trans. 1, 1994, 1969.
8. R. J. Parry, S. V. Mhaskar, M.-T. Lin, A. E. Walker and R. Mafoti, Can. J. Chem., 1994, 86.
9. J. M. Humphrey, J. A. Hart and A. R. Chamberlin, Bioorg. Med. Chem. Lett., 1995,5, 1315.
10. N. M. Kelly, R. G. Reid, C. L. Willis and P. L. Winton, Tetrahedron Lett., 1996, 37, 1517.
11. For reviews of chiral auxiliaries derived from amino acids including Evans' auxiliaries see: (a) D. J. Ager, I. Prakash and D. R. Sacad, Chem. Rev., 1996,96, 835;
12. (b) A. Studer, Synthesis, 1996, 793.
13. A. Sutherland and C. L. Willis, Tetrahedron Lett., 1997,38, 1837.
14. (a) D. A. Evans, J. Bartroli and T. L. Shih, J. Am. Chem. Soc., 1981, 103, 2127;
15. (b) D. A. Evans, M. D. Ennis and D. J. Mathre, J. Am. Chem. Soc., 1982, 104, 1737.
16. D. A. Evans, T. C. Britton and J. A. Ellman, Tetrahedron Lett., 1987, 28,6141.
17. For reviews see: (a) A. J. L. Cooper, J. Z. Ginos and A. Meister, Chem. Rev., 1993,83,321;
18. (b) L. Kovacs, Reel. Trav. Chim. Pays-Bas, 1993, 112, 471.
19. H. H. Wasserman and B.-W. Ho, J. Org. Chem., 1994,59,4364.
20. Z. Shaked and G. M. Whitesides, J. Am. Chem. Soc., 1980, 102, 7104.
21. J. M. Bentley, H. J. Wadsworth and C. L. Willis, J. Chem. Soc., Chem. Commun., 1995, 231.
22. K. Yonaha and K. Soda, Adv. Biochem. Eng. Biotechnol., 1986, 96;
23. Y. Asano, A. Yamada, Y. Kato, K. Yamaguchi, Y. Hindo, K. Hirai and K. Kondo, J. Org. Chem., 1990, 55, 5567;
24. C. Wandrey, R. Wichman and A. S. Jandel, Enzyme Eng., 1982, 6, 61.
25. N. K. Kochetkov, A. M. Likhosherstov and V. M. Kulakov, Tetrahedron, 1969,25, 2313.
26. T. Oshima and K. Soda, Eur. J. Biochem., 1970, 100, 29;
27. B. C. O'Neill, J. Probert, G. Reid, R. Stephen, T. Wang, C. L. Willis and P. Winton, Tetrahedron Lett., 1994, 35, 6533.
28. M. Miyamoto, K. Morita, Y. Kawamatsu, K. Kawahima and N. Nakanishi, Tetrahedron, 1967, 23, 411;
29. J. H. Dodd, R. S. Garigipati and S. M. Weinreb, J. Org. Chem., 1982,47,4045.
30. S. Mitsui, T. Kamaishi, T. Imaizumi and I. Takaniura, Chem. Abstr., 1963,59,11569e;
31. T. Kamaishi and S. Mitsui, Chem. Abstr., 1966, 65, 2326e;
32. S. Mitsui and A. Kanai, Chem. Abstr., 1966, 65, 2101g;
33. S. Mitsu and A. Kanai, Chem. Abstr. 1966, 65, 17006f;
34. S. Mitsui I and I. Imai, Chem. Abstr., 1967, 67, 43934h;
35. K. Harada and T. Munegurami, Bull. Chem. Soc. Jpn., 1983, 56, 2774.
36. For further examples of the reduction of 2-keto acids with LDHs see: D. Bur, M. A. Luyten, H. Wynn, L. R. Provencher, J. B. Jones, M. Gold, J. D. Preisen, A. R. Clarke and J. J. Holbrook, Can. J. Chem., 1989, 67, 1065;
37. M.-J. Kim and G. M. Whitesides, J. Am. Chem. Soc., 1988,110,2959;
38. M.-J. Kim and J. Y. Kim, J. Chem. Soc., Chem. Commun., 1991, 326;
39. B. L. Hirschbein and G. M. Whitesides, J. Am. Chem. Soc., 1982, 104, 4458;
40. Y. S. Tsantrizos, J. F. Lunetta, M. Boyd, L. D. Fader and M.-C. Wilson, J. Org. Chem., 1997, 62, 5451;
41. G. Casy, T. V. Lee and H. Lovell, Tetrahedron Lett., 1992, 33, 817.
42. For further details on the use of LB-hicDH to prepare (R)-2-hydroxy acids see: A. Sutherland and C. L. Willis, J. Org. Chem., 1998, 63, 7764 and references cited therein.
43. G. Bhalay, S. Clough, L. McLaren, A. Sutherland and C. L. Willis, J. Chem. Soc., Perkin Trans. 1, 2000, in press.
44. A. Sutherland and C. L. Willis, Bioorg. Med. Chem. Lett., 1999, 9, 1941.
45. See for example: H. Kluender, F.-C. Huang, A. Fritzberg, H. Schnoes and C. J. Sih, J. Am. Chem. Soc, 1974, 96, 4054.
46. J. E. Baldwin, R. M. Adlington, N. P. Crouch, N. J. Turner and C. J. Schofield, J. Chem. Soc., Chem. Commun., 1989, 1141.
47. J. E. Baldwin, R. M. Adlington, N. P. Crouch, L. C. Mellor, N. Morgan, A. M. Smith and J. D. Sutherland, Tetrahedron, 1995, 51, 4089.
48. M. D. -Fletcher, J. R. Harding, R. A. Hughes, N. M. Kelly, H. Schmalz, A. Sutherland and C. L. Willis, J. Chem. Soc., Perkin Trans. 1, 2000, 42.
49. (a) W. Oppolzer, R. J. Mills, W. Pachinger and T. Stevenson, Heh. Chim. Acta, 1986, 69, 1542;
50. (b) M. Vandewalle, J. Van der Eycken, W. Oppolzer and C. Vullioud, Tetrahedron, 1986, 42, 4035;
51. W. Oppolzer, G. Poli, A. J. Kingma, C. Starkemann and G. Bernardinelli, Helv. Chim. Acta, 1987,70,2201;
52. W. Oppolzer, A. J. Kingma and G. Poli, Tetrahedron, 1989, 45, 479;
53. (e) W. Oppolzer and A. J. Kingma, Heh. Chim. Acta, 1989, 72, 1337;
54. (/) W. Oppolzer, PureAppl. Chem., 1990, 62, 1241;
55. (g) W. Oppolzer, Tetrahedron, 1987, 43, 1969.
56. W. Oppolzer, O. Tamura and J. Deerberg, Heh: Chim. Acta, 1992, 75, 1965;
57. R.Voges, in Synthesis and Applications of Isotopically Labelled Compounds 1994, eds. J. Allen and R. Voges, Wiley, New York, 1995, p. 1.
58. R. M. Moriarty and I. Prakaash, Synth. Commun., 1985, 15, 649.
59. D. A. Evans, T. C. Britton, R. L. Borrow and J. F. Dellania, Tetrahedron, 1988, 44, 5525.
60. J. M. Herbert, J. Labelled Compd. Radiopharm., 1998,41, 859.
61. J. A. MacRitchie, A. Silcock and C. L. Willis, Tetrahedron: Asymmetry, 1997,8, 3895.
62. F. L. Weisenborn, J. W. Bolger, D. B. Rosen, L. T. Mann, Jr., L. Johnson and H. L. Holmes, J. Am. Chem. Soc., 1954, 76, 1792.
63. S. Trippelt and D. M. Walker, J. Chem. Soc., 1959, 3874;
64. G. P. Schiemenz and H. Engelhard, Chem. Ber., 1961, 94, 578.
65. W. A. Huffman and A. W. Ingersoll, J. Am. Chem. Soc., 1951, 73, 3366.
66. J. P. Greenstein, S. M. Birnbaum and M. C. Ottey, J. Biol. Chem., 1953,204, 307.
67. M. Wintz, L. Boch-Frankenthal, N. Izumiya, S. M. Birnbaum, C. G. Baker and J. P. Greenstein, J. Am. Chem. Soc., 1956, 78, 2423.
68. D. F. Elliot, J. Chem. Soc., 1950, 62.
69. L. C. Vining and W. A. Tabor, Can. J. Chem., 1957, 35, 1109.
70. K. Arvid and J. Wretlind, Acta Chem. Scand., 1952, 6, 611.
71. R. S. Ward, A. Pelter, D. Goubet and M. C. Pritchard, Tetrahedron: Asymmetry, 1995,6,469.
72. W. Oppolzer and J.-P. Barras, Helv. Chim. Acta, 1987, 70, 1666.