Synthesis of secondary amines via N-(benzoyloxy)amines and organoboranes

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 803-806

  Phanstiel IV, O ^a   Wang, Q X ^a   Powell, D H ^b   Ospina, M P ^b   Leeson, B A ^a  

^a UNIVERSITY OF CENTRAL FLORIDA   (United States)

^b University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BORANE DERIVATIVE; N (BENZOYLOXY)AMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033524874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981613l     Document Type: Article

References (23)

1. (a) Bergeron, R. J.; Feng, Y.; Weimar, W. R.; McManis, J. S.; Dimova, H.; Porter, C.; Raisler, B.; Phanstiel, O. J. Med. Chem. 1997, 40, 1475-1494.
2. (b) Carboni, B.; Vaultier, M. Bull. Soc. Chim. Fr. 1995, 132, 1003-1008.
3. Rathke, M. W.; Inoue, N.; Varma, K. R.; Brown, H. C. J. Am. Chem. Soc. 1966, 88, 2870.
4. Kabalka, G. W.; Sastry, K. A. R.; McCollum, G. W.; Yoshioka, H. J. Org. Chem. 1981, 46, 4296.
5. Chloroamine: Brown, H. C.; Heydkamp, W. R.; Breuer, E.; Murphy, W. S. J. Am. Chem. Soc. 1964, 86, 3565.
6. Brown, H. C.; Malhotra, S. V.; Ramachandan, P. V. Tetrahedron: Asymmetry 1996, 7, 3527-3534.
7. Primary amines via hydrazoic acid: Kabalka, G. W.; Henderson, D. A.; Varma, R. S. Organometallics 1987, 6, 1369-1370.
8. Primary amines via O-mesitylenesulfonylhydroxylamine: Tamura, Y.; Minamikawa, J.; Fujii, S.; Ikeda, M. Synthesis 1974, 196.
9. Protected amines via organoborane technology: (a) Yang, R.; Dai, L. Synthesis 1993, 481-482. (b) Jigajinni, V. B.; Pelter, A.; Smith, K. Tetrahedron Lett. 1978, 181-182. (c) Genet, J.-P.; Hajicek, J.; Bischoff, L.; Greek, C. Tetrahedron Lett. 1992, 33, 2677.
10. Protected amines via organoborane technology: (a) Yang, R.; Dai, L. Synthesis 1993, 481-482. (b) Jigajinni, V. B.; Pelter, A.; Smith, K. Tetrahedron Lett. 1978, 181-182. (c) Genet, J.-P.; Hajicek, J.; Bischoff, L.; Greek, C. Tetrahedron Lett. 1992, 33, 2677.
11. Protected amines via organoborane technology: (a) Yang, R.; Dai, L. Synthesis 1993, 481-482. (b) Jigajinni, V. B.; Pelter, A.; Smith, K. Tetrahedron Lett. 1978, 181-182. (c) Genet, J.-P.; Hajicek, J.; Bischoff, L.; Greek, C. Tetrahedron Lett. 1992, 33, 2677.
12. Negisihi, E.; Idecavage, M. K. Org. React. NY 1985, 33, 1.
13. Dialkylamine synthesis: Kabalka, G. W.; Wang, Z. Organometallics 1989, 8, 1093-1095 and references therein.
14. Organic azides: Suzuki, A.; Sono, S.; Itoh, M.; Brown, H. C.; Midland, M. J. Am. Chem. Soc. 1971, 93, 4329.
15. Secondary amines via organic azides: Brown, H. C.; Midland, M. M., Levy, A. B. J. Am. Chem. Soc. 1972, 94, 2114-2115.
16. N-chloroamine in situ: Kabalka, G. W.; McCollum, G. W.; Kunda, S. A. J. Org. Chem. 1984, 49, 1656-1657.
17. Wang, Q. X.; King, J.; Phanstiel IV, O. J. Org. Chem., 1997, 62, 8104-8108.
18. Biloski, A. J.; Ganem, B. Synthesis 1983, 537-538.
19. Milewska, M. J.; Chimiak, A. Synthesis 1990, 233-234.
20. Wang, Q. X.; Phanstiel, O., IV. J. Org. Chem. 1998, 63, 1491-1495.
21. 1H NMR spectral data for N-ethylamine derivatives; for compound 8, see: Pienemann, T.; Schafer, H.-J. Synthesis 1987, 1005-1007. 10:
22. 1H NMR spectral data for N-ethylamine derivatives; for compound 8, see: Pienemann, T.; Schafer, H.-J. Synthesis 1987, 1005- 1007. 10: Ponchert, C. J.; Campbell, J. R. The Aldrich Library of NMR Spectra 1974, Vol. V, 97. 11: Ishihara, Y.; Kato, K.; Goto, G. Chem. Pharm. Bull. 1991, 39, 3225-3235.
23. 1H NMR spectral data for N-ethylamine derivatives; for compound 8, see: Pienemann, T.; Schafer, H.-J. Synthesis 1987, 1005- 1007. 10: Ponchert, C. J.; Campbell, J. R. The Aldrich Library of NMR Spectra 1974, Vol. V, 97. 11: Ishihara, Y.; Kato, K.; Goto, G. Chem. Pharm. Bull. 1991, 39, 3225-3235.