A convenient synthesis of N-alkyl-(E)-1-alkenesulfonamides

Synlett

Volumn , Issue 2, 1998, Pages 186-188

  Tozer, Matthew J ^a   Woolford, Alison J A ^a   Linney, Ian D ^a  

^a James Black Foundation   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001946519     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1609     Document Type: Article

References (20)

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2. (b) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem. Int. Ed. Engl. 1995, 34, 1763.
3. (c) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem. Int. Ed. Engl. 1995, 34, 1765.
4. (d) Gennari, C.; Salom, B.; Potenza, D.; Longari, C.; Fioravazo, E.; Carugo, O.; Sardone, N. Chem. Eur. J. 1996, 2, 644.
5. Mladenova, M.; Gaudemar-Bardone, F. Phosphorus, Sulfur, and Silicon 1991, 62, 257.
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7. Oliver J. E.; DeMilo, A. B. Synthesis 1975, 321.
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10. Thompson, M. E. J. Org. Chem. 1984, 49, 1700.
11. An example being: Roth, B. D.; Roark, W. H.; Picard, J. A.; Stanfield, R. L.; Bousley, R. F.; Anderson, M. K.; Hamelehle, K. L.; Homan, R.; Krause, B. R. Bioorg. Med. Chem. Lett. 1995, 5, 2367.
12. Examples of 2-hydroxyalkanesulfonamide synthesis based on Thompson's method: (a) Grunder-Klotz, E.; Ehrhardt, J.-D. Synlett 1991, 800.
13. (b) Poss, M. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 7291.
14. (c) Poss, M. A.; Reid, J. A.; Free, C. A.; Rogers, W. L.; Weber, H.; Ryono, D. E.; Dejneka, T.; DeForrest, J. M.; Waldron, T. L.; Brittain, R. J.; Weller, H. N.; Cimarusti, M. P.; Petrillo, E. W. Bioorg. Med. Chem. Lett. 1993, 3, 2739.
15. (d) Davis, F. A.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1993, 58, 4890.
16. (e) Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823.
17. There is precedent for OBoc behaving as a leaving group in similar circumstances, with a lactam rather than a sulfonamide: Schmidt, U.; Riedl, B.; Haas, G.; Griesser, H.; Vetter, A.; Weinbrenner, S. Synthesis 1993, 216.
18. 5S: C 58.03, H 8.05, N 2.94%; Found: C 58.05, H 8.26, N 3.04%.
19. 2S: C 60.40, H 7.89, N 3.91%; Found: C 60.64, H 7.74, N 3.91%.
20. For a perspective of the area: Lee, Y. S.; Ryu, E. K.; Yun, K.-Y.; Kim, Y. H. Synlett 1996, 247. Table. The Synthesis of Vinylsulfonamides.