Oxidative C-C bond cleavage of N-alkoxycarbonylated cyclic amines by sodium nitrite in trifluoroacetic acid

Tetrahedron Letters

Volumn 49, Issue 47, 2008, Pages 6728-6731

  Onomura, Osamu ^a   Moriyama, Atsushi ^a   Fukae, Kazuhiro ^a   Yamamoto, Yutaka ^a   Maki, Toshihide ^a   Matsumura, Yoshihiro ^a   Demizu, Yosuke ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Amino acid; Carbon carbon cleavage; Cyclic amines; Sodium nitrite; Trifluoroacetic acid

Indexed keywords

4 AMINO 3 HYDROXYBUTYRIC ACID; AMINE; CARBON; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; OMEGA AMINO ACID; PIPERIDINE DERIVATIVE; SODIUM NITRITE; TRIFLUOROACETIC ACID;

ARTICLE; CARBON CARBON BOND; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ENANTIOMER; OXIDATION KINETICS; REACTION ANALYSIS;

EID: 53149089755     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.067     Document Type: Article

References (24)

1. Some examples:. Deno N.C., and Messer L.A. J. Chem. Soc., Chem. Commun. (1976) 1051
2. Stewart R., and Spitzer U.D. Can. J. Chem. 56 (1978) 1273-1279
3. Nomura K., and Uemura S. J. Chem. Soc. Chem. Commun. (1994) 129-130
4. Murahashi S., Komiya N., Oda Y., Kuwabara T., and Naota T. J. Org. Chem. 65 (2000) 9186-9193
5. Onomura O., Yamamoto Y., Moriyama N., Iwasaki F., and Matsumura Y. Synlett (2006) 2415-2418
6. 2 in TFA:. Ongayi O., Fronczek F.R., and Vincente M.G. Chem. Commun. (2003) 2298-2299
7. Matsumura Y., Yamamoto Y., Moriyama N., Furukubo S., Iwasaki F., and Onomura O. Tetrahedron Lett. 45 (2004) 8221-8224
8. Ru porphyrin/2,6-dichloropyridine N-oxide system-catalyzed oxidative ring cleavage of N-acylated cyclic amines has been reported:. Ito R., Umezawa N., and Higuchi T. J. Am. Chem. Soc. 127 (2005) 834-835
9. Ru-catalyzed oxidative ring cleavage of N-alkoxycarbonyl α,β-unsaturated cyclic amines, see:
10. Torii S., Inokuchi T., and Kondo K. J. Org. Chem. 50 (1985) 4980-4982
11. Sakagami H., Kamikubo T., and Ogasawara O. Synlett (1997) 221-222
12. Ozonolysis of them, see:. Gnad F., Poleschak M., and Reiser O. Tetrahedron Lett. 45 (2004) 4277-4280
13. Degradative autooxidation of N-acyl-3-piperidinones, see:. Schirmann P.J., Matthews R.S., and Dittmer D.C. J. Org. Chem. 48 (1983) 4426-4427
14. 2O (10 equiv) in TFA did not proceed at all. {A figure is presented}.
15. 3): 2.16 V for 1a, 2.10 V for 1e, 2.33 V for 1f.
16. {A figure is presented}.
17. Shono T., Hamaguchi H., and Matsumura Y. J. Am. Chem. Soc. 97 (1975) 4264-4268
18. The oxidation of 1a under nitrogen atmosphere gave 2a in 25% yield along with recovered 1a in 69% yield.
19. + 323.1005: found 323.0993. Optical purity was determined by HPLC analysis employing a Daicel Chiralcel OJ-H column (4.6 mm ø, 250 mm). n-Hexane/ethanol = 5:1, 0.1% TFA, wavelength: 220 nm, flow rate: 1.0 mL/ min, retention time: 27.3 min (R), 30.9 min (S).
20. 3): 2.17 V for 10h.
21. + 365.1474: found 365.1474. Optical purity was determined by HPLC analysis employing a Daicel Chiralcel OJ-H column (4.6 mm ø, 250 mm), n-Hexane/ethanol = 5:1, 0.1% TFA, wavelength: 220 nm, flow rate: 1.0 mL/min, retention time: 10.1 min (R), 10.9 min (S).
22. 3): 2.21 V for 11.
23. + 185.0688: found 185.0667. Optical purity was determined by HPLC analysis employing a Daicel Chiralcel OD-H column (4.6 mm ø × 250 mm). n-Hexane/ethanol = 15:1, wavelength: 220 nm, flow rate: 1.0 mL/min, retention time: 27.4 min (S), 29.3 min (R).
24. Chemoenzymatic approach:. Felluga F., Pitacco G., Prodan M., Pricl S., Visintin M., and Valentin E. Tetrahedron: Asymmetry 12 (2001) 3241-3249