Lewis acid catalysis in heterolysis reactions of glycol ether radicals mimicking diol dehydratase-catalyzed reactions

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4511-4514

  Miranda, Neil ^a   Xu, Libin ^a   Newcomb, Martin ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; GLYCOL; HYDROLYASE; LEWIS ACID; RADICAL;

ARTICLE; BINDING AFFINITY; CATALYSIS; ENZYME DEGRADATION; FRAGMENTATION REACTION; LASER; PHOTOLYSIS; REACTION ANALYSIS;

CATALYSIS; ETHERS; FREE RADICALS; MOLECULAR MIMICRY; PROPANEDIOL DEHYDRATASE;

EID: 10044248460     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0481131     Document Type: Article

References (31)

1. Toraya, T. Chem. Rev. 2003, 103, 2095-2127.
2. Toraya, T. Chem. Rec. 2002, 2, 352-366.
3. Buley, A. L.; Norman, R. O. C.; Pritchett, R. J. J. Chem. Soc., B 1966, 849-852.
4. Walling, C.; Johnson, R. A. J. Am. Chem. Soc. 1975, 97, 2405-2407.
5. Lee, H. A., Jr.; Abeles, R. H. J. Biol. Chem. 1963, 238, 2367-2373.
6. Toraya, T.; Sugimoto, Y.; Tamao, Y.; Shimizu, S.; Fukui, S. Biochemistry 1971, 10, 3475-3484.
7. Shibata, N.; Masuda, J.; Tobimatsu, T.; Toraya, T.; Suto, K.; Morimoto, Y.; Yasuoka, N. Structure 1999, 7, 997-1008.
8. 9
9. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901-3924.
10. Newcomb, M.; Miranda, N. J. Org. Chem. 2004, 69, 6515-6520.
11. Le Tadic-Biadatti, M.-H.; Newcomb, M. J. Chem. Soc., Perkin Trans. 2 1996, 1467-1473.
12. Martinez, F. N.; Schlegel, H. B.; Newcomb, M. J. Org. Chem. 1998, 63, 3618-3623.
13. Newcomb, M.; Tanaka, N.; Bouvier, A.; Tronche, C.; Horner, J. H.; Musa, O. M.; Martinez, F. N. J. Am. Chem. Soc. 1996, 118, 8505-8506.
14. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921.
15. Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
16. Tronche, C.; Martinez, F. N.; Horner, J. H.; Newcomb, M.; Senn, M.; Giese, B. Tetrahedron Lett. 1996, 37, 5845-5848.
17. Choi, S. Y.; Crich, D.; Horner, J. H.; Huang, X. H.; Newcomb, M.; Whitted, P. O. Tetrahedron 1999, 55, 3317-3326.
18. Bagnol, L.; Horner, J. H.; Newcomb, M. Org. Lett 2003, 5, 5055-5058.
19. Horner, J. H.; Taxil, E.; Newcomb, M. J. Am. Chem. Soc. 2002, 124, 5402-5410.
20. Horner, J. H.; Bagnol, L.; Newcomb, M. J. Am. Chem. Soc. 2004, 126, 14979-14987.
21. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358.
22. Ha, C.; Musa, O. M.; Martinez, F. N.; Newcomb, M. J. Org. Chem. 1997, 62, 2704-2710.
23. Feng, H.; Kavrakova, I. K.; Pratt, D. A.; Tellinghuisen, J.; Porter, N. A. J. Org. Chem. 2002, 67, 6050-6054.
24. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029-11030.
25. Porter, N. A.; Wu, J. H. L.; Zhang, G. R.; Reed, A. D. J. Org. Chem. 1997, 62, 6702-6703.
26. Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554-6565.
27. Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929-2932.
28. Beckwith, A. L. J.; Crich, D.; Duggan, P. J.; Yao, Q. W. Chem. Rev. 1997, 97, 3273-3312.
29. Crich, D. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 188-206.
30. Crich, D.; Shirai, M.; Rumthao, S. Org. Lett. 2003, 5, 3767-3769.
31. Crich, D.; Ranganathan, K.; Neelamkavil, S.; Huang, X. H. J. Am. Chem. Soc. 2003, 125, 7942-7947.