Chirospecific synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-immo-L-xylitol via one-pot cyclisation

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 17, 1998, Pages 2877-2880

  Kim, Jin Hyo ^a   Yang, Min Suk ^a   Lee, Woo Song ^a   Park, Ki Hun ^a  

^a Gyeongsang National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748639758     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803342k     Document Type: Article

References (19)

1. (a) G. W. J. Fleet, S. J. Nicolas, P. W. Smith, S. V. Evans, L. E. Fellows and R. J. Nash, Tetrahedron Lett., 1985, 26, 3127;
2. (b) N. Asano, K. Oseki, H. Kizu and K. Matsui, J. Med. Chem., 1994, 37, 3701;
3. (c) N. Asano, H. Kizu, K. Oseki, E. Tomioka, K. Matsui, M. Okamoto and M. Baba, J. Med. Chem., 1995, 38, 2349.
4. (a) R. J. Nash, E. A. Bell and J. M. Williams, Phytochemistry, 1985, 24, 1620;
5. (b) J. Furukawa, S. Okuda, K. Saito and S. I. Hatanaka, Phytochemistry, 1985, 24, 593.
6. For a preparation of D-iminoarabinitol (a) G. W. J. Fleet and P. W. Smith, Tetrahedron, 1986, 42, 5685;
7. (b) T. Ziegler, A. Straub and F. Effenberger, Angew. Chem., Int. Ed. Engl., 1988, 27, 716;
8. (c) G. W. J. Fleet and D. R. Witty, Tetrahedron: Asymmetry, 1990, 1, 119;
9. (d) T. Kajimoto, L. Chen, K. K.-C. Liu and C.-H. Wong, J. Am. Chem. Soc., 1991, 113, 6687.
10. For a preparation of D-iminoxylitol (e) J. G. Buchanan, K. W. Lumbard, R. J. Sturgeon, D. K. Thompson and R. H. Wightman, J. Chem. Soc., Perkin Trans. 1, 1990, 699;
11. (f) Q. Meng and M. Hesse, Helv. Chim. Acta, 1991, 74, 445;
12. (g) Y. Huang and D. R. Dalton, J. Org. Chem., 1997, 62, 372.
13. W. D. Lubell and H. Rapoport, J. Am. Chem. Soc., 1987, 109, 236.
14. (a) R. Csuk, M. Hugener and A. Vasella, Helv. Chim. Acta, 1988, 71, 609;
15. (b) M. Gerspacher and H. Rapoport, J. Org. Chem., 1991, 56, 3700.
16. K. H. Park, Y. J. Yoon and S. G. Lee, Tetrahedron Lett., 1994, 35, 9737.
17. (a) F. R. Cruickshank and S. W. Benson, J. Phys. Chem., 1969, 73, 733;
18. (b) A. R. Vaino and W. A Szarek, Chem. Commun., 1996, 2351.
19. I. Pastuszak, R. J. Molyneux, L. F. James and A. D. Elbein, Biochemistry, 1990, 29, 1886.