N,Se-acetals: Easy preparation and application to radical mediated EPC synthesis

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9199-9202

  Stojanovic, Aleksandar ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; RADICAL;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030590953     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02160-0     Document Type: Article

References (20)

1. 1. For a recent review on 1-amino and 1-amidoalkyl radicals see: Renaud, P.; Giraud, L. Synthesis 1996, 913-926.
2. 2. Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689-2692.
3. 3. See for exemple: Nedugov, A. N.; Pavlova, N. N.; Usmanova, Z. R. Zh. Org. Khim. 1994, 30, 70-72. Anciaux, A.; Eman, A.; Dumont, W.; Van Ende, D.; Krief, A. Tetrahedron Lett. 1975, 1613-1616. Pollak, I. E.; Grillot, G. F. J. Org. Chem. 1966, 31, 3514-3516. Grillot, G. F.; Felton, H. R.; Garrett, B. R.; Greenberg, H.; Green, R.; Clementi, R.; Moskowitz, M. J. Am. Chem. Soc. 1954, 76, 3969-3971.
4. 3. See for exemple: Nedugov, A. N.; Pavlova, N. N.; Usmanova, Z. R. Zh. Org. Khim. 1994, 30, 70-72. Anciaux, A.; Eman, A.; Dumont, W.; Van Ende, D.; Krief, A. Tetrahedron Lett. 1975, 1613-1616. Pollak, I. E.; Grillot, G. F. J. Org. Chem. 1966, 31, 3514-3516. Grillot, G. F.; Felton, H. R.; Garrett, B. R.; Greenberg, H.; Green, R.; Clementi, R.; Moskowitz, M. J. Am. Chem. Soc. 1954, 76, 3969-3971.
5. 3. See for exemple: Nedugov, A. N.; Pavlova, N. N.; Usmanova, Z. R. Zh. Org. Khim. 1994, 30, 70-72. Anciaux, A.; Eman, A.; Dumont, W.; Van Ende, D.; Krief, A. Tetrahedron Lett. 1975, 1613-1616. Pollak, I. E.; Grillot, G. F. J. Org. Chem. 1966, 31, 3514-3516. Grillot, G. F.; Felton, H. R.; Garrett, B. R.; Greenberg, H.; Green, R.; Clementi, R.; Moskowitz, M. J. Am. Chem. Soc. 1954, 76, 3969-3971.
6. 3. See for exemple: Nedugov, A. N.; Pavlova, N. N.; Usmanova, Z. R. Zh. Org. Khim. 1994, 30, 70-72. Anciaux, A.; Eman, A.; Dumont, W.; Van Ende, D.; Krief, A. Tetrahedron Lett. 1975, 1613-1616. Pollak, I. E.; Grillot, G. F. J. Org. Chem. 1966, 31, 3514-3516. Grillot, G. F.; Felton, H. R.; Garrett, B. R.; Greenberg, H.; Green, R.; Clementi, R.; Moskowitz, M. J. Am. Chem. Soc. 1954, 76, 3969-3971.
7. 4. Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2693-2694.
8. 5. Arya, P.; Wayner, D. D. M. Tetrahedron Lett. 1991, 32, 6265-6268.
9. Arya, P.; Lesage, M.; Wayner, D. D. M. Tetrahedron Lett. 1991, 32, 2853-2856.
10. 6. N,O-acetals can also be obtained from amides by electrochemical oxidation: Shono, T. Electrochemistry as a New Tool in Organic Synthesis; Springer: Berlin, 1984. The efficiency of this approach is however weakend by the formation of regioisomers when unsymmetric secondary amines are employed.
11. 7. See for exemple: Burnett, D. A.; Choi, J. K.; Hart, D. J.; Tsai, Y. M. J. Am. Chem. Soc. 1984, 106, 8201-8209 and references cited therein.
12. 8. Böhme, H.; Hartke, K. Chem. Ber. 1963, 96, 600-603.
13. 9. Grignon, J.; Pereyre, M. J. Organomet. Chem. 1973, 61, C33-C35. Keck, G.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079-4094.
14. 9. Grignon, J.; Pereyre, M. J. Organomet. Chem. 1973, 61, C33-C35. Keck, G.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079-4094.
15. 10. Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831-2843.
16. 4), concentration and chromatography of the crude product on silica gel afforded the desired N,Se-acetals.
17. 12. For a typical procedure, see: Renaud, P.; Stojanovic, A. Tetrahedron Lett. 1996, 37, 2569-2572.
18. 1,3 strain model in radical chemistry see: Giese, B.; Damm, W.; Batra, R. Chemtracts: Org. Chem. 1994, 7, 355-370. For examles with amino substituted radicals, see ref. 12 and: Damm, W.; Hoffmann, U.; Macko, L.; Neuburger, M.; Zehnder, M.; Giese, B. Tetrahedron 1994, 50, 7029-7048. Lesage, M.; Arya, P. Synlett 1996, 237-238.
19. 1,3 strain model in radical chemistry see: Giese, B.; Damm, W.; Batra, R. Chemtracts: Org. Chem. 1994, 7, 355-370. For examles with amino substituted radicals, see ref. 12 and: Damm, W.; Hoffmann, U.; Macko, L.; Neuburger, M.; Zehnder, M.; Giese, B. Tetrahedron 1994, 50, 7029-7048. Lesage, M.; Arya, P. Synlett 1996, 237-238.
20. 1,3 strain model in radical chemistry see: Giese, B.; Damm, W.; Batra, R. Chemtracts: Org. Chem. 1994, 7, 355-370. For examles with amino substituted radicals, see ref. 12 and: Damm, W.; Hoffmann, U.; Macko, L.; Neuburger, M.; Zehnder, M.; Giese, B. Tetrahedron 1994, 50, 7029-7048. Lesage, M.; Arya, P. Synlett 1996, 237-238.