Preparation of racemic and enantiopure arenesulfonimidoyl azoles - New compounds chiral on sulfur

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 149, Issue , 1999, Pages 179-206

  Kluge, Ralph ^a   Hocke, Heiko ^a   Schulz, Manfred ^a   Schilke, Frank ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Arenesulfonimidoyl azoles; Asymmetric hexavalent sulfur compounds; Diastereo and enantioselectivity; HPLC separation of enantiomers; Synthesis

Indexed keywords

EID: 0033234137     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426509908037031     Document Type: Article

References (26)

1. H. A. Staab, Angew. Chem. 74, 407 (1962).
2. a) N. Katagiri, K. Hakura, S. A. Narany, J. Am. Chem. Soc. 97, 7332 (1975).
3. b) S. S. Jones, B. Rayner, C. B. Reese, A. Ubasawa, Tetrahedron 36, 3075 (1980).
4. c) R. J. Ferner, P. C. Tyler, J. Chem. Soc. Perkin Trans, 1, 295 (1985).
5. d) J. F. O'Connell, H. Rapoport, J. Org. Chem. 57, 4775 (1992).
6. e) M. Gerspacher, H. Rapoport, J. Org. Chem. 56, 3700 (1991).
7. a) R. Kluge, M. Schulz, S. Liebsch, Tetrahedron 52, 2957 (1996)
8. b) R Kluge, M. Schulz, S. Liebsch, Tetrahedron 52, 5773 (1996).
9. M. R. Jones, D. J. Cram, J. Am. Chem. Soc. 96, 2183 (1974).
10. a) E. U. Jonsson, C. R. Johnson, J. Am. Chem. Soc. 93, 5308 (1971).
11. b) C. R. Johnson, A. Wambgans, J. Org. Chem. 44, 2278 (1979).
12. c) C. R. Johnson, E. U. Jonsson, C. C. Bacon, J. Org. Chem. 44, 2055 (1979).
13. Y. H. Chiang, J. Luloff, E. Schipper, J. Org. Chem. 34, 2397 (1969).
14. J. Jacobus, K. Mislow, Chem. Commun., 253 (1968).
15. S)-13c was prepared analogously from (S)-phenylethylamine: A. Nudelman, D. J. Cram, J. Am. Chem. Soc. 90, 3869 (1968).
16. C. R. Johnson, K. B. Bis, J. H. Cantillo, J. Org. Chem. 48, 1 (1983)
17. Crystallographic data (excluding structure factors) for the structure can be requested from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany) specifying the deposit number CSD 410651 (fax: 49-7247-808-666, e-mail : crysdata@fiz-karlsruhe.de).
18. M. Mikolajczyk, J. Drabowicz, Top in Stereochem. 13, 333 (1982).
19. O. W. Steward, J. Organomet. Chem. 109, 179 (1976).
20. a) E. L. Mutterties, Acc. Chem. Res. 3, 266 (1970)
21. b) D. J. Cram, J. Day, D. R. Rayner, D. M. Schriltz, D. J. Duchamp, D. C. Garwood, J. Am. Chem. Soc. 92, 7369 (1970).
22. a) J. C. Martin, T. M. Balthazor, J. Am. Chem. Soc. 99, 152 (1977)
23. b) P. Huszty, I. Kapowits, A. Kucsman, L. Radic, Tetrahedron Lett., 1853 (1978).
24. R. R. Holmes, Acc. Chem. Res. 12, 257 (1979).
25. R. Kluge, H. Hocke, M. Schulz, Tetrahedron: Asymmetry 8, 2513 (1997).
26. P. G. Cooksen, G. B. Deacon, Austr. J. Chem. 24, 1599 (1971).