Synthesis of novel, optically active, heterocyclic amino alcohols through desymmetrization of a C2-symmetric cyclic sulfate

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6921-6922

  Kim, B Moon ^a   Bae, Sung Jin ^a   Seomoon, Gunn ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; HETEROCYCLIC AMINE;

ARTICLE; DRUG SYNTHESIS; HYDROXYLATION; ISOMERISM; STRUCTURE ACTIVITY RELATION;

CHIRON;

EID: 0032541722     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01453-1     Document Type: Article

References (20)

1. 1. (a) Jones, J. O.; McElhinney, R. S. J. Chem. Research (S) 1982, 116.
2. (b) Jones, J. O.; McElhinney, R. S. Ibid 1984, 146.
3. (c) Märki, F.; Breitenstein, W.; Beriger, E.; Bernasconi, R.; Caravatti, G.; Francis, J. E.; Paioni, R.; Wehrli, H. U.; Wiederkehr, R. Agents Actions 1993, 38, 202.
4. (d) Ghosh, A. K.; Thompson W. J.; McKee, S. P.; Duong, T. T.; Lyle, T. A.; Chen, J. C.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1993, 36, 292.
5. (e) Ghosh, A. K.; Thompson W. J.; Lee, H. Y.; McKee, S. P.; Munson, P. M.; Duong, T. T.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1993, 36, 924.
6. (f) Kim, B. M.; Lee, H.-Y.; Munson, P. M.; Guare, J. P.; McDonough, C. Tetrahedron Lett. 1993, 34, 6517.
7. (g) Murabayashi, A.; Ostsuka, S.; Tanimoto, N. Jpn. Kokai Tokkyo Koho JP 05 58,995, 1993.
8. (h) Walsh, D. A.; Shamblee, D. A. US Patent 4,254,135, 1981.
9. 2. (a) Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1993, 34, 5273.
10. (b) Schaus, S. E.; Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1997, 62, 4197.
11. 3. For desymmetrization strategy in organic synthesis, see (a) Ho, T, L. Symmetry, A Basis for Synthesis Design; Wiley: NY, 1995.
12. (b) Ho, T, L. Tactics of Organic Synthesis,; Wiley: NY, 1994; pp. 337-373.
13. 4. (a) Yun, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
14. (b) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
15. (c) Lohray, B. B.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2623.
16. 5. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
17. 6. Hanessian, S. Total Synthesis of Natural Products: The 'Chiron' Approach; Pergamon Press: Oxford, 1983.
18. 13C NMR, and HRMS) data.
19. 8. Vanhessche, K. P. M.; Wang, Z. M.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 3469.
20. 9. Although cyclic sulfate 5 has been prepared using sulfuryl chloride, exploration of the synthetic utility of 5 has not been reported. See, Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517.