Direct construction of 1,3-diaxial diol derivatives by C-H hydroxylation

Organic Letters

Volumn 11, Issue 16, 2009, Pages 3630-3632

  Kasuya, Satoshi ^a   Kamijo, Shin ^a   Inoue, Masayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; DIOXIRANE; EPOXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; HYDROXYLATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; COMBINATORIAL CHEMISTRY TECHNIQUES; EPOXY COMPOUNDS; HYDROXYLATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 68949091820     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901367m     Document Type: Article

References (41)

1. For recent reviews, see: (a) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
2. (b) Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L., Jr. Chem. Rev. 2004, 104, 939.
3. (c) Activation and Functionalization of C-H Bonds; Goldberg, K. I., Goldman, A. S., Eds.; American Chemical Society: Washington, DC, 2004.
4. (d) Hanbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005; Vols. 1 and 2.
5. (e) Davies, H. M. L.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 3518.
6. (f) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
7. (g) Christmann, M. Angew. Chem., Int. Ed. 2008, 47, 2740.
8. (h) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
9. For recent representative examples, see: (a) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
10. (b) Kaufman, M. D.; Grieco, P. A.; Bougie, D. W. J. Am. Chem. Soc. 1993, 115, 11648.
11. (c) Groves, J. T.; Bonchio, M.; Carofiglio, T.; Shalyaev, K. J. Am. Chem. Soc. 1996, 118, 8961.
12. (d) Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. Chem. Commun. 1997, 861.
13. (e) Kim, C.; Chen, K.; Kim, J.; Que, L., Jr. J. Am. Chem. Soc. 1997, 119, 5964.
14. (f) Breslow, R.; Huang, Y.; Zhang, X.; Yang, J. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 11156.
15. (g) Arnone, A.; Foletto, S.; Metrangolo, P.; Pregnolato, M.; Resnati, G. Org. Lett. 1999, 1, 281.
16. (h) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
17. (i) Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
18. (j) Chen, M. S.; White, M. C. Science 2007, 318, 783.
19. (k) Chen, K.; Richter, J. M.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 7247.
20. (l) Chen, K.; Baran, P. S. Nature 2009, 459, 824.
21. (m) Litvinas, N. D.; Brodsky, B. H.; Du Bois, J. Angew. Chem., Int. Ed. 2009, 48, 4513.
22. For recent reviews on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
23. (b) Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Org. React. 2002, 61, 219.
24. (c) Yang, D. Acc. Chem. Res. 2004, 37, 497.
25. (d) Curci, R.; D'Accolti, L.; Fusco, C. Acc. Chem. Res. 2006, 39, 1.
26. (e) Adam, W.; Zhao, C.-G.; Jakka, K. Org. React. 2007, 69, 1.
27. (f) Wong, O. A.; Shi, Y. Chem. Rev. 2008, 108, 3958.
28. Yang reported the pioneering works on δ-selective intramolecular oxidation of unactivated C-H bonds.
29. (a) Yang, D.; Wong, M.-K.; Wang, X.-C.; Tang, Y.-C. J. Am. Chem. Soc. 1998, 120, 6611.
30. (b) Wong, M.-K.; Chung, N.-W.; He, L.; Yang, D. J. Am. Chem. Soc. 2003, 125, 158.
31. (c) Wong, M.-K.; Chung, N.-W.; He, L.; Wang, X.-C.; Yan, Z.; Tang, Y.-C.; Yang, D. J. Org. Chem. 2003, 68, 6321.
32. (a) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347.
33. (b) Germanas, J.; Aubert, C.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1991, 113, 4006.
34. (c) Taillier, C.; Gille, B.; Bellosta, V.; Cossy, J. J. Org. Chem. 2005, 70, 2097.
35. Moriguchi, T.; Endo, T.; Takata, T. J. Org. Chem. 1995, 60, 3523.
36. Trifluoromethyl ketones of compounds 1A-F were in equilibrium with their corresponding hydrate forms.
37. Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887.
38. 3 significantly decreased the yield, presumably due to the base sensitivity of the -alkoxy ketone.
39. 2·EDTA solution = 3/2 (0.01 M) at rt for 1 d] did not give 1,3-dimethyl-cyclohexane-1,3-diol 7A, and the starting material was recovered.
40. 3. (a) Murray, R. W.; Jeyaraman, R.; Mohan, L. J. Am. Chem. Soc. 1986, 108, 2470.
41. (b) Mello, R.; Fiorentino, M.; Fusco, C.; Curci, R. J. Am. Chem. Soc. 1989, 111, 6749.