Oxidative rearrangement of imidazoles with dimethyldioxirane

Organic Letters

Volumn 6, Issue 5, 2004, Pages 735-738

  Lovely, Carl J ^a   Du, Hongwang ^a   He, Yong ^a   Dias, H V Rasika ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXANE DERIVATIVE; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CURTIUS REARRANGEMENT; DIASTEREOISOMER; DRUG STRUCTURE; OXIDATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 1642414157     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036403w     Document Type: Article

References (34)

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10. For other approaches to the cyclopentane core, see: (a) Overman, L. E.; Rogers, B. N.; Tellow, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159. (b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (c) Belanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880. (d) Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Loewe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203.
11. For other approaches to the cyclopentane core, see: (a) Overman, L. E.; Rogers, B. N.; Tellow, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159. (b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (c) Belanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880. (d) Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Loewe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203.
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17. For related rearrangements, see: (a) Cushing, T. D.; Sanz-Cervera, J. F. ; Williams, R. M. J. Am. Chem. Soc. 1996, 115, 557. (b) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147. Ganesan, A.; Wang, H. J. Org. Chem. 2000, 65, 4685.
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25. (14) A third, as yet unidentified product was obtained from this reaction.
26. (15) Stereochemical descriptors endo/exo are used to indicate the orientation of the imidazolone carbonyl moiety with respect to the azabicyclo[3.3.0]octane.
27. 13C NMR chemical shift of the imidazolone carbonyl carbon (δ = 180.4), which is consistent with those obtained for other 5-imidazolones prepared in this study, a number of which were characterized by X-ray crystallography.
28. (17) See Supporting Information for the preparation of these substrates.
29. (18) Although we have no direct evidence, it is reasonable to assume a similar orientation for the hydroxymethyl group in 16b since it would avoid a steric clash with the 4-OTBS moiety.
30. 2 at 75 psi, HOAc, 95°C) in a minor modification of a literature procedure. Butula, I. Croat. Chem. Acta 1973, 45, 297.
31. (20) These compounds were prepared from 1-benzyltetrahydrobenzimidazole. For details see Supporting Information.
32. Klutchko, S.; Hodges, J. C.; Blankley, C. J.; Colbry, N. L. J. Heterocycl. Chem. 1991, 28, 97. This material was obtained as a 1:1 mixture of 4-and 5-regioisomers
33. The exact mechanism of this oxidative rearrangement is unknown at this time, and alternative mechanisms are certainly possible; however, it is convenient to formulate the rearrangement with the participation of the 3a,7a-epoxide and the resulting zwitterionic intermediate. See also: Wasserman, H. H.; Yoo, J. U.; DeSimone, R. W. J. Am. Chem. Soc. 1995, 117, 9772.
34. (23) Inquiries regarding X-ray determinations should be directed to Dr. Simon Bott (University of Houston) at sbott@uh.edu.