Synthesis of alkoxylamines by alkoxide amination with 3,3'-Di-tert- butyloxaziridine

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6528-6529

  Choong, Ingrid C ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; AZTREONAM; OXIME DERIVATIVE; ROXITHROMYCIN;

AMINATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032887346     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990490h     Document Type: Article

References (22)

1. Tuchscherer, G. Tetrahedron Lett. 1993, 34, 8419.
2. Rose, K. J. Am. Chem. Soc. 1994, 116, 30.
3. Shao, J.; Tam, J. P. J. Am. Chem. Soc. 1995, 117, 3893.
4. Canne, L. E.; Ferré-D́Amaré, A. R.; Burley, S. K.; Kent, S. B. H. J. Am. Chem. Soc. 1995, 117, 2998.
5. Cornish, V. W.; Hahn, K. M.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 8150.
6. Rodriguez, E. C.; Marcaurelle, L. A.; Bertozzi, C. R. J. Org. Chem. 1998, 63, 7134.
7. MDL Drug Data Report, MDL Information Systeme, Inc., San Leandro, CA.
8. Grochowski, E.; Jurczak, J. Synthesis 1976, 682.
9. Kim, J. N.; Kim, K. M.; Ryu, E. K. Synth. Commun. 1992, 22, 1427.
10. Theilacker, W.; Ebke, K. Angew. Chem. 1956, 68, 303.
11. Truitt, P.; Long, L. M.; Mattison, M. J. Am. Chem. Soc. 1948, 70, 9.
12. Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239.
13. Sheradsky, T. J. Heterocycl. Chem. 1967, 4, 413.
14. Paquette, L. A. J. Am. Chem. Soc. 1963, 85, 3288.
15. Theilacker, W. Angew. Chem. 1960, 72, 498.
16. Theilacker, W.; Ebke, K.; Seidl, L.; Schwerin, S. Angew. Chem. 1963, 75, 208.
17. Castellino, A. J.; Rapoport, H. J. Org. Chem. 1983, 49, 1348.
18. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 319, 195.
19. Andreae, S.; Schmitz, E. Synthesis 1991, 327.
20. Amination of methanol by 1 under acid catalysis has been reported to give cyclohexanone oxime O-methyl ether in 40% yield. No experimental details were provided. Schmitz, E. Dreiringe mit zwei Heteroatomen; Springer-Verlag: Berlin, 1967.
21. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131.
22. Hudson, R. F.; Lawson, A. J.; Record, K. A. F. J. Chem. Soc., Chem. Commun. 1975, 322.