Studies on the chemistry of the chiral nitronic acid and nitronic esters

Tetrahedron Asymmetry

Volumn 8, Issue 21, 1997, Pages 3585-3589

  Kang, Fu An ^a   Yin, Cheng Lie ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID; ESTER; HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; OXIME;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0031566711     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0957-4166(97)00478-3     Document Type: Article

References (19)

1. 1. For reviews, see: (a) Feuer, H. The Chemistry of the Nitro and Nitroso Groups, Wiley: New York, 1969.
2. (b) Breuer, E. The Chemistry of Amino, Nitro so and Nitro Compounds and their Derivatives, Wiley: New York, 1982.
3. (c) Torssell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH: New York, 1988.
4. 2. (a) Kang, F. A.; Yin, C. L.; She, S. W. Chin. Sci. Bull. 1996, 41, 1847.
5. (b) Kang, F. A.; Yin, C. L.; She, S. W. J. Org Chem. 1996, 61, 5523.
6. 3. (a) Kang, F. A.; Yin, C. L. J. Chem. Soc., Chem. Commun. 1997, 579.
7. (b) Kang, F. A.; Yin, C. L. Tetrahedron in press.
8. 4. (a) Kang, F. A.; Yin, C. L. J. Am. Chem. Soc. 1997, 119, 8562.
9. (b) Kang, F. A.; Yin, C. L. Prog. Nat. Sci. in press.
10. 5. Feringa, B. L.; de Jong, J. C. J. Org. Chem. 1988, 53, 1125.
11. 6. Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1964, 86, 2681.
12. 7. This reaction condition was reported for the conversion of nitro to carbonyl, see: Kornblum, N.; Wade, P. J. Org. Chem. 1973, 38, 1418, but in this case the reaction gives 5 rather than 6.
13. 8. This reaction condition was described for the transformation of nitro to carbonyl, see: Keinan, E.; Mazur, Y. J. Am. Chem. Soc. 1977, 99, 3861, however in this case the reaction produces 4 rather than 6.
14. 9. Interestingly, this ozonolysis does not occur between -78 and -20deg;C, until the temperature is raised to 0°C. Previous ozonolyses were often carried out under strict conditions, see: (a) McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259.
15. (b) Lehr, F.; Gonnermann, J.; Seebach, D. Helv. Chim. Acta 1979, 62, 2274.
16. -1.
17. 11. The chiral nitronic esters 3 melt in boiling water, and solidify when they become cool without any change.
18. 12. Gree, R.; Carrie, R. Tetrahedron Lett. 1971, 4117.
19. 13. Kang, F. A.; Yin, H. Y.; Yin, C. L. Chin. Sci. Bull. 1997, 42, 1628.