Ruthenium tetroxide oxidation of cyclic N-acylamines by a single layer method: formation of ω-amino acids

Tetrahedron Letters

Volumn 49, Issue 17, 2008, Pages 2786-2788

  Kaname, Mamoru ^a   Yoshifuji, Shigeyuki ^a   Sashida, Haruki ^a  

^a HOKURIKU UNIVERSITY   (Japan)

Author keywords

Amino acid; Cyclic N acylamine; Double layer system; Ruthenium tetroxide oxidation; Single layer system

Indexed keywords

ACETIC ACID ETHYL ESTER; AMINE; BUTANOL; CYCLIC N ACYLAMINE; LACTAM; N ACYL LACTAM; OMEGA AMINO ACID; OXIDE; RUTHENIUM TETROXIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; OXIDATION;

EID: 40949126885     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.127     Document Type: Article

References (24)

1. Lee D.G., and van den Engh M. In: Trahanovsky W.S. (Ed). Oxidation in Organic Chemistry (1973), Academic Press, New York Part B, Chapter 4 and Part D
2. Bernd P. Synthesis (2005) 2453-2472
3. Sheehan J.C., and Tulis R.W. J. Org. Chem. 39 (1974) 2264-2267
4. Carlsen P.H.J., Katsuki T., Martin V.S., and Sharpless K.B. J. Org. Chem. 46 (1981) 3936-3938
5. Yoshifuji S., Arakawa Y., and Nitta Y. Chem. Pharm. Bull. 33 (1985) 5042-5047
6. Yoshifuji S., Tanaka K., Kawai T., and Nitta Y. Chem. Pharm. Bull. 33 (1985) 5515-5521
7. Yoshifuji S., Tanaka K., Kawai T., and Nitta Y. Chem. Pharm. Bull. 34 (1986) 3873-3878
8. Yoshifuji S., Tanaka K., and Nitta Y. Chem. Pharm. Bull. 33 (1985) 1749-1751
9. Tanaka K., Yoshifuji S., and Nitta Y. Chem. Pharm. Bull. 35 (1987) 364-369
10. Yoshifuji S., Tanaka K., and Nitta Y. Chem. Pharm. Bull. 35 (1987) 2994-3000
11. 4 requires long reaction time:. Nakata H. Tetrahedron 19 (1963) 1959-1963
12. Yoshifuji S., Matsumoto H., Tanaka K., and Nitta Y. Tetrahedron Lett. 21 (1980) 2963-2964
13. Tanaka K., Yoshifuji S., and Nitta Y. Chem. Pharm. Bull. 34 (1986) 3879-3884
14. Kaname M., and Yoshifuji S. Tetrahedron Lett. 33 (1992) 8103-8104
15. Yoshifuji S., and Kaname M. Chem. Pharm. Bull. 43 (1995) 1302-1306
16. Yoshifuji S., and Kaname M. Chem. Pharm. Bull. 43 (1995) 1617-1620
17. Ito R., Umezawa N., and Higuchi T. J. Am. Chem. Soc. 127 (2005) 834-835
18. 12 were identical with authentic samples, respectively.
19. 3): δ 25.3 (t, C3), 28.41 and 79.2 (q and s, t-Bu), 31.3 (t, C2), 39.9 (t, C4), 51.7 (q, OMe), 156.0 (s, NC{double bond, long}O), 173.8 (s, C1).
20. Cantacuzene D., and Guerreiro C. Tetrahedron 45 (1989) 741-748
21. Todd D., and Teich S. J. Am. Chem. Soc. 75 (1953) 1895-1900
22. Barluenga J., Foubelo F., Fananas F.J., and Yus M. Tetrahedron 45 (1989) 2183-2192
23. Giovannini A., Savoia D., and Umani-Ronchi A. J. Org. Chem. 54 (1989) 228-234
24. Mundy B.P., Larsen B.R., McKenzie L.F., and Braden G. J. Org. Chem. 37 (1972) 1635-1636