Preparation of optically active 3-substituted piperidines via ring expansion: Synthesis of 4-amino- and 4-fluoro-1,4,5-trideoxy-1,5-imino-D-ribitol and 1,5-dideoxy-1,5-imino-D-ribitol

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 8, 1996, Pages 803-808

  Kim, Dae Kee ^a   Kim, Ganghyeok ^a   Kim, Young Woo ^a  

^a Sunkyong Industries   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001224647     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000803     Document Type: Article

References (19)

1. (a) G. C. Look, C. H. Fotsch and C.-H. Wong, Acc. Chem. Res., 1993, 26, 182;
2. (b) T. Hudlicky, J. Rouden, H. Luna and S. Allen, J. Am. Chem. Soc., 1994, 116, 5099;
3. (c) T. Tschamber, F. Backenstrass, M. Neuburger, M. Zehnder and J. Streith, Tetrahedron, 1994, 50, 1135;
4. (d) F. Backenstrass, J. Streith and T. Tschamber, Tetrahedron Lett., 1990, 31, 2139;
5. (e) C. R. Johnson, A. Golebiowski, H. Sundram, M. W. Miller and R. L. Dwaihy, Tetrahedron Lett., 1995, 36, 653;
6. (f) B. B. Shankar, M. P. Kirkup, S. W. McCombie and A. K. Ganguly, Tetrahedron Lett., 1993, 34, 7171;
7. (g) R. C. Bernotas, G. Papandreou, J. Urbach and B. Ganem, Tetrahedron Lett., 1990, 31, 3393;
8. (h) J. Di, B. Rajanikanth and W. A. Szarek, J. Chem. Soc., Perkin Trans. 1, 1992, 2151;
9. (i) N. Asano, K. Oseki, H. Kizu and K. Matsui, J. Med. Chem., 1994, 37, 3701.
10. (a) K. M. Robinson, H. E. Begovic, B. L. Rhinehart, E. W. Heineke, J.-B. Ducep, P. R. Kastner, F. N. Marshall and C. Danzin, Diabetes, 1991, 40, 825;
11. (b) A. B. Hughes and A. J. Rudge, Nat. Prod. Rep 1994, 11, 135.
12. I. M. Jones and G. S. Jacob, Nature, 1991, 352, 198;
13. D. A. Winker and G. J. Holan, J. Med. Chem., 1989, 32, 2084.
14. M. J. Humphries, K. Matsumoto, S. L. White and K. Olden, Cancer Res., 1986, 46, 5215.
15. M. P. Dale, H. E. Ensley, K. Kern, K. A. R. Sastry and L. D. Byers, Biochemistry, 1985, 24, 3530.
16. N. Asano, K. Oseki, E. Tomioka, H. Kizu and K. Matsui, Carbohydr. Res., 1994, 259, 243.
17. J. Cossy, C. Dumas, P. Michel and D. G. Pardo, Tetrahedron Lett., 1995, 36, 549.
18. R. R. Schmidt, J. Karg and W. Guilliard, Chem. Ber., 1977, 110, 2433;
19. P. D. Kane and J. Mann, J. Chem. Soc., Perkin Trans. 1, 1984, 657.