Oxidative cleavage of p-methoxybenzyl ethers with methyl(trifluoromethyl) dioxirane

Organic Letters

Volumn 7, Issue 21, 2005, Pages 4665-4667

  Paquette, Leo A ^a   Kreilein, Matthew M ^a   Bedore, Matthew W ^a   Friedrich, Dirk ^b  

^a OHIO STATE UNIVERSITY   (United States)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27144548055     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051856h     Document Type: Article

References (13)

1. Kocienski, P. J. Protecting Groups, 3rd ed.; Georg Thieme Verlag: Stuttgart, 2004; pp 257-269.
2. Paquette, L. A.; Hofferberth, J. E. J. Org. Chem. 2003, 68, 2266.
3. Kreilein, M. M. Ph.D. Dissertation, The Ohio State University, 2005.
4. (a) Adam, W.; Curci, R.; Edward, J. O. Acc. Chem. Res. 1989, 22, 205.
5. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187.
6. (c) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, p 1.
7. Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887.
8. Takahata, H.; Banba, Y.; Sasatani, H.; Nemoto, H.; Kato, A.; Adachi, I. Tetrahedron 2004, 60, 8199.
9. (a) Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. J. Am. Chem. Soc. 1954, 76, 4749.
10. (b) Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. Tetrahedron 1963, 19, 247.
11. (a) Rogic, M. M.; Demmin, M. M.; Hammond, W. B. J. Am. Chem. Soc. 1976, 98, 7441.
12. (b) Demmin, M. M.; Rogic, M. M. J. Org. Chem. 1980, 45, 4210.
13. The oxidation of catechol to the muconic acids is also known: McKague, A. B. Synth. Commun. 1999, 29, 1463.