A new concise stereoselective method for the preparation of a β- hydroxyfurfurylamine derivative and synthesis of 1-deoxyazasugar isomers

Tetrahedron Asymmetry

Volumn 10, Issue 18, 1999, Pages 3649-3657

  Liao, Li Xin ^a   Wang, Zhi Min ^a   Zhang, Hong Xing ^b   Zhou, Wei Shan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033461804     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00382-1     Document Type: Article

References (24)

1. Schmidt, D. D.; Frommer, W.; Muller, L.; Truscheit, E. Naturwissenschaften 1979, 66, 584.
2. Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327.
3. Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135.
4. (a) Zhou, W. S.; Lu, Z. H.; Wang, Z. M. Tetrahedron Lett. 1991, 32, 1467;
5. (b) Zhou, W. S.; Lu, Z. H.; Wang, Z. M. Tetrahedron 1993, 49, 2641.
6. (a) Xu, Y. M.; Zhou, W. S. Tetrahedron Lett. 1996, 37, 1461;
7. (b) Xu, Y. M.; Zhou, W. S. J. Chem. Soc., Perkin Trans 1 1997, 741.
8. Altenbach, H. J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983-4984.
9. (a) Xu, Y. M.; Jiang, W.; Zhou, W. S. Chinese J. Org. Chem., in press;
10. (b) Bushey, M. L.; Haukaas, M. H.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2984;
11. (c) Li, G.; Chang, H. T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
12. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768.
13. Taniguchi, T.; Nakamura, K.; Ogasawara, K. Synlett 1996, 971.
14. Schmidt, U.; Werner, J. Synthesis 1986, 986.
15. The e.e. values were determined by HPLC analysis on Chiralcel OJ column with n-hexane-iPrOH as the eluent.
16. Chang, H. T.; Sharpless, K. B. Tetrahedron Lett. 1996, 37, 3219.
17. 6 is unambiguously proven to be cis.
18. 6 is unambiguously proven to be cis.
19. 6 is unambiguously proven to be cis.
20. 3.
21. Lu, Z. H.; Zhou, W. S. J. Chem. Soc., Perkin Trans. 1 1993, 593.
22. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592.
23. Yang, C. F.; Xu, Y. M.; Liao, L. X.; Zhou, W. S. Tetrahedron Lett. 1998, 39, 9227.
24. Yang, C. F.; Liao, L. X.; Xu, Y. M.; Zhang, H. X.; Xia, P.; Zhou, W. S. Tetrahedron: Asymmetry 1999, 10, 2311.