A very mild and chemoselective oxidation of alcohols to carbonyl compounds

Organic Letters

Volumn 3, Issue 19, 2001, Pages 3041-3043

  De Luca, Lidia ^a   Giacomelli, Giampaolo ^a   Porcheddu, Andrea ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000810296     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016501m     Document Type: Article

References (17)

1. Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed.; Wiley-Interscience: New York, 2001; pp 1514-1517.
2. Jurczak, J.; Golebiowski, A, Chem. Rev. 1989, 89, 149.
3. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J. L. J. Org. Chem. 1996, 61, 7452 and references therein.
4. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
5. (a) Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395. (b) Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M. J. Org. Chem. 1999, 64, 8962. Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett 2000, 275. De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534. (e) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 1519.
6. (a) Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395. (b) Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M. J. Org. Chem. 1999, 64, 8962. Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett 2000, 275. De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534. (e) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 1519.
7. (a) Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395. (b) Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M. J. Org. Chem. 1999, 64, 8962. Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett 2000, 275. De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534. (e) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 1519.
8. (a) Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395. (b) Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M. J. Org. Chem. 1999, 64, 8962. Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett 2000, 275. De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534. (e) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 1519.
9. (a) Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395. (b) Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M. J. Org. Chem. 1999, 64, 8962. Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett 2000, 275. De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534. (e) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 1519.
10. Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559.
11. Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029.
12. Marcacci, F.; Giacomelli, G.; Menicagli, R. Gazz. Chim. Ital. 1980, 110, 195.
13. On the basis of this datum, it is possible to conclude that this oxidation method proceeds with better stereochemistry than the DCC-DMSO system.6
14. (a) Sharma, R. P.; Gore, M. G.; Akhtar, M. J. Chem. Soc. Chem. Commun. 1979, 875. (b) Soucek, M.; Urban, J Collect. Czech. Chem. Commun. 1995, 60, 693.
15. (a) Sharma, R. P.; Gore, M. G.; Akhtar, M. J. Chem. Soc. Chem. Commun. 1979, 875. (b) Soucek, M.; Urban, J Collect. Czech. Chem. Commun. 1995, 60, 693.
16. Hiegel and Nalbandy (Hiegel, G. A.; Nalbandy, M. Synth. Commun. 1992, 22, 1595) reported that in combination with pyridine secondary alcohols are rapidly oxidized to ketones by trichloroisocyanuric acid.
17. Finn, P. J.; Gibson, N. J.; Fallon, R.; Hamilton, A.; Brown, T. Nucleic Acids Res. 1996, 24, 3357.