Simple synthesis of variously N-protected α-aminomethanesulfinate salts

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5648-5649

  Dujols, Frédéric J M ^a   Mulliez, Michel E ^a  

^a UFR des Sciences Exactes et Naturelles   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011903685     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9516648     Document Type: Article

References (23)

1. Gennari, C.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2067 and references cited therein.
2. Mulliez, M. Tetrahedron 1981, 37, 2021.
3. Garrigues, B.; Mulliez, M. Synthesis 1988, 810.
4. Garrigues, B.; Mulliez, M. Phosphorus, Sulfur Silicon 1991, 57, 203.
5. Mulliez, M.; Naudy, C. Tetrahedron 1993, 49, 2469.
6. Mulliez, M.; Naudy, C. Tetrahedron 1994, 50, 5401.
7. Leurquin, F.; Mulliez, M. Phosphorus, Sulfur Silicon 1994, 92, 201.
8. 6 we observed that with the zinc salt attack is dramatically diverted on the sulfur atom, probably as a result of complexation of nitrogen with the zinc cation. With the sodium salt one cannot exclude such an attack followed by fast transfer to nitrogen.
9. Toyle, J. In The Chemistry of Sulfinic Acids Esters and Their Derivatives; Patai, S., Ed.; John Wiley and Sons: New York, 1991; pp 469-470.
10. Electrophilic amination is advantageously performed directly on the sodium salts 4, in water, the resulting insoluble sulfonamide derivatives 3 being easily separated by filtration (Mulliez, M. Unpublished results). For example, 4a leads to the known 3 (R′ = H): Etienne, A.; Le Berre, A.; Lonchambon, G.; Lochey, G.; Cucumel, B. Bull. Soc. Chim. Soc. Fr. 1974, 580. Gilmore, W. F.; Yeih, M. M.; Smith, R. B. J. Org. Chem. 1986, 43, 4784.
11. Electrophilic amination is advantageously performed directly on the sodium salts 4, in water, the resulting insoluble sulfonamide derivatives 3 being easily separated by filtration (Mulliez, M. Unpublished results). For example, 4a leads to the known 3 (R′ = H): Etienne, A.; Le Berre, A.; Lonchambon, G.; Lochey, G.; Cucumel, B. Bull. Soc. Chim. Soc. Fr. 1974, 580. Gilmore, W. F.; Yeih, M. M.; Smith, R. B. J. Org. Chem. 1986, 43, 4784.
12. Electrophilic amination is advantageously performed directly on the sodium salts 4, in water, the resulting insoluble sulfonamide derivatives 3 being easily separated by filtration (Mulliez, M. Unpublished results). For example, 4a leads to the known 3 (R′ = H): Etienne, A.; Le Berre, A.; Lonchambon, G.; Lochey, G.; Cucumel, B. Bull. Soc. Chim. Soc. Fr. 1974, 580. Gilmore, W. F.; Yeih, M. M.; Smith, R. B. J. Org. Chem. 1986, 43, 4784.
13. This is the case with HOSu but not with HCl. Therefore, introduction of the protecting group via the chloride is restricted to the sodium salt 4.
14. Frankel, M.; Ladkany, D.; Gilon, C.; Wolman, Y. Tetrahedron Lett. 1966, 4765.
15. Wünsch, E.; Graf, W.; Keller, O.; Wersin, G. Synthesis 1986, 958.
16. Moroder, L.; Halett, A.; Wünsch, E.; Keller, O.; Wersin, G. Hoppe-Seyler's Z. Physiol. Chem. 1976, 357, 1651.
17. Nefkens, G. H. L.; Tesser, G. I.; Nivard, R. J. F. Rec. Trav. Chim. Pays-Bas 1960, 79, 688.
18. Richardson, A. G.; Pierce, J. S.; Reid, E. E. J. Am. Chem. Soc. 1952, 74, 4011. The oxalyl group can repetitively be used successively as a protecting and an activating group: Mulliez, M.; Royer, J. Tetrahedron 1984, 40, 5143.
19. Richardson, A. G.; Pierce, J. S.; Reid, E. E. J. Am. Chem. Soc. 1952, 74, 4011. The oxalyl group can repetitively be used successively as a protecting and an activating group: Mulliez, M.; Royer, J. Tetrahedron 1984, 40, 5143.
20. Staab, H. A. Angew. Chem., Int. Ed. Engl. 1962, 351.
21. Ramage, R.; Hopton, D.; Parott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1984, 1357.
22. -.
23. 18 9f.