An efficient methodology to substituted furans via oxidation of functionalized α-diazo-β-ketoacetates

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2093-2096

  Truong, Phong ^a   Xu, Xinfang ^a   Doyle, Michael P ^a  

^a Bldg 142   (United States)

Author keywords

Diazoacetate; Dimethyldioxirane; Furan; Oxidation; Vicinal tricarbonyl

Indexed keywords

3 METHOXYFURAN 2 CARBOXYLATE; ACETIC ACID DERIVATIVE; ALDEHYDE; ALPHA DIAZO BETA KETOACETATE; CARBOXYLIC ACID DERIVATIVE; DIMETHYLDIOXIRANE; FURAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CATALYSIS; MUKAIYAMA REACTION; OXIDATION; QUANTITATIVE ANALYSIS; SYNTHESIS;

EID: 79953231972     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.166     Document Type: Article

References (22)

1. (a) Rubin, M. D. Chem. Rev. 1975, 75, 177-202;
2. (b) Wasserman, H. H.; Parr, H. Acc. Chem. Res. 2004, 37, 687-701.
3. De Neufville, R.; von Pechmann, H. Chem. Ber. 1890, 23, 3375-3387.
4. Rubin, M.; Gleiter, R. Chem. Rev. 2000, 100, 1121-1164.
5. (a) Wasserman, H. H.; Han, W. T. Tetrahedron Lett. 1984, 25, 3743-3746;
6. (b) Wasserman, H. H.; Han, W. T. Tetrahedron Lett. 1984, 25, 3747-3750;
7. (c) Wasserman, H. H.; Han, W. T. J. Am. Chem. Soc. 1985, 5, 1444-1446.
8. (a) Wasserman, H. H.; Kuo, G. H. Tetrahedron Lett. 1989, 30, 873-876;
9. (b) Wasserman, H. H.; Amici, R.; Frechette, R.; Van Duzer, J. Tetrahedron Lett. 1989, 30, 869-872;
10. (c) Wasserman, H. H.; Lombardo, L. J. Tetrahedron Lett. 1989, 30, 1725-1728;
11. (d) Wasserman, H. H.; Amici, R. J. Org. Chem. 1989, 54, 5843-5844.
12. (a) Wasserman, H. H.; Fukuyama, J.; Murugesan, N.; van Duzer, J.; Lombardo, L.; Rotello, V.; McCarthy, K. J. Am. Chem. Soc. 1989, 111, 371-372;
13. (b) Wasserman, H. H.; Cook, J. D.; Fukuyama, J. M.; Rotello, V. M. Tetrahedron Lett. 1989, 30, 1721-1724.
14. Wasserman, H. H.; Cook, J. D.; Vu, C. B. J. Org. Chem. 1990, 55, 1701-1702.
15. Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783-9786.
16. Doyle, M.; Zhou, L. Org. Lett. 2010, 12, 796-799.
17. Regitz, M.; Maas, G. Diazo Compounds: Properties and Synthesis; Academic Press: Orlando, FL, 1986.
18. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998. Chapter 1.
19. (a) Gleiter, R.; Schang, P. Angew. Chem., Int. Ed. 1980, 19, 715-716;
20. (b) Detering, J.; Martin, H. D. Angew. Chem., Int. Ed. 1988, 27, 695-698.
21. Saba, A. Synth. Commun. 1994, 24, 695-699.
22. Adam, W.; Bialas, J.; Hadjiarapoglou, L. P. Chem. Ber. 1991, 24, 2377-2378. Procedure for the preparation of DMDO.