Baeyer-Villiger oxidation promoted by reaction of peracids with cyclic oxocarbenium ions generated in situ from internal hemiketals

Organic Letters

Volumn 2, Issue 12, 2000, Pages 1717-1719

  Hunt, Kevin W ^a   Grieco, Paul A ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; MACROLIDE; REACTIVE OXYGEN METABOLITE; STEROID;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

KETONES; MACROLIDES; OXIDATION-REDUCTION; REACTIVE OXYGEN SPECIES; STEROIDS;

EID: 0034658874     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000068j     Document Type: Article

References (25)

1. Krow, G. R. Org. React. 1993, 43, 251. Hassall, C. H. Org. React. 1957, 9, 73. Bolm, C. In Advances in Catalytic Processes, Vol. 2; Doyle, M. P., Ed.; JAI Press: Greenwich, 1997; p 43. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737. Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1198.
2. Krow, G. R. Org. React. 1993, 43, 251. Hassall, C. H. Org. React. 1957, 9, 73. Bolm, C. In Advances in Catalytic Processes, Vol. 2; Doyle, M. P., Ed.; JAI Press: Greenwich, 1997; p 43. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737. Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1198.
3. Krow, G. R. Org. React. 1993, 43, 251. Hassall, C. H. Org. React. 1957, 9, 73. Bolm, C. In Advances in Catalytic Processes, Vol. 2; Doyle, M. P., Ed.; JAI Press: Greenwich, 1997; p 43. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737. Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1198.
4. Krow, G. R. Org. React. 1993, 43, 251. Hassall, C. H. Org. React. 1957, 9, 73. Bolm, C. In Advances in Catalytic Processes, Vol. 2; Doyle, M. P., Ed.; JAI Press: Greenwich, 1997; p 43. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737. Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1198.
5. Krow, G. R. Org. React. 1993, 43, 251. Hassall, C. H. Org. React. 1957, 9, 73. Bolm, C. In Advances in Catalytic Processes, Vol. 2; Doyle, M. P., Ed.; JAI Press: Greenwich, 1997; p 43. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737. Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1198.
6. Monopermaleic, monoperpthalic, monopersulfuric, m-chloroperbenzoic, trifluoroperacetic, peracetic, and benzeneperoxyseleninic acids were employed with and without the addition of Lewis acids.
7. Lapalme, R.; Borschberg, H. J.; Soucy, P.; Deslongchamps, P. Can. J. Chem. 1979, 57, 3272. Suzuki, M.; Takada, H.; Noyori, R. J. Org. Chem. 1982, 47, 902. Yamada, T.; Takahashi, K.; Kato, K. Chem. Lett. 1991, 641.
8. Lapalme, R.; Borschberg, H. J.; Soucy, P.; Deslongchamps, P. Can. J. Chem. 1979, 57, 3272. Suzuki, M.; Takada, H.; Noyori, R. J. Org. Chem. 1982, 47, 902. Yamada, T.; Takahashi, K.; Kato, K. Chem. Lett. 1991, 641.
9. Lapalme, R.; Borschberg, H. J.; Soucy, P.; Deslongchamps, P. Can. J. Chem. 1979, 57, 3272. Suzuki, M.; Takada, H.; Noyori, R. J. Org. Chem. 1982, 47, 902. Yamada, T.; Takahashi, K.; Kato, K. Chem. Lett. 1991, 641.
10. Upon exposure of 2 to trifluoroperacetic acid or m-chloroperbenzoic acid in the presence of boron trifluoride etherate at ambient temperature, 2 undergoes debenzylation leading to the formation of hemiketal i in ca. 40% yield. (matrix presented)
11. 7 have shown that oxocarbenium ions generated from mixed acetals or ketals react with m-chloroperbenzoic acid, giving rise to lactones and orthocarbonates, respectively.
12. Grieco, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett. 1978, 419.
13. Bailey, W. F.; Shih, M.-J. J. Am. Chem. Soc. 1982, 104, 1769 . Also see: Gaoni, Y. J. Chem. Soc. C 1968, 2925.
14. Bailey, W. F.; Shih, M.-J. J. Am. Chem. Soc. 1982, 104, 1769 . Also see: Gaoni, Y. J. Chem. Soc. C 1968, 2925.
15. 2 -78 °C, 6 h; (2) TPAP (5 mol %), NMO (2.0 equiv), 4 Å m.s., 7 h; (3) TBAF, HOAc, THF, 0 °C → rt, 14 h].
16. (b) Prepared from diol iii employing the sequence outlined in ref 8a. (matrix presented)
17. Acylation of hydroperoxy ketals followed by Criegee rearrangement of the resultant acyl peroxide has been reported: Criegee, R. Chem. Ber. 1944, 77, 772. Criegee, R. Justus Liebigs Ann. Chem. 1948, 560, 127. Hedaya, E.; Winstein, S. J. Am. Chem. Soc. 1967, 89, 1661. Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363. Ziegler, F. E.; Wester, R. T. Tetrahedron Lett. 1984, 25, 617.
18. Acylation of hydroperoxy ketals followed by Criegee rearrangement of the resultant acyl peroxide has been reported: Criegee, R. Chem. Ber. 1944, 77, 772. Criegee, R. Justus Liebigs Ann. Chem. 1948, 560, 127. Hedaya, E.; Winstein, S. J. Am. Chem. Soc. 1967, 89, 1661. Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363. Ziegler, F. E.; Wester, R. T. Tetrahedron Lett. 1984, 25, 617.
19. Acylation of hydroperoxy ketals followed by Criegee rearrangement of the resultant acyl peroxide has been reported: Criegee, R. Chem. Ber. 1944, 77, 772. Criegee, R. Justus Liebigs Ann. Chem. 1948, 560, 127. Hedaya, E.; Winstein, S. J. Am. Chem. Soc. 1967, 89, 1661. Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363. Ziegler, F. E.; Wester, R. T. Tetrahedron Lett. 1984, 25, 617.
20. Acylation of hydroperoxy ketals followed by Criegee rearrangement of the resultant acyl peroxide has been reported: Criegee, R. Chem. Ber. 1944, 77, 772. Criegee, R. Justus Liebigs Ann. Chem. 1948, 560, 127. Hedaya, E.; Winstein, S. J. Am. Chem. Soc. 1967, 89, 1661. Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363. Ziegler, F. E.; Wester, R. T. Tetrahedron Lett. 1984, 25, 617.
21. Acylation of hydroperoxy ketals followed by Criegee rearrangement of the resultant acyl peroxide has been reported: Criegee, R. Chem. Ber. 1944, 77, 772. Criegee, R. Justus Liebigs Ann. Chem. 1948, 560, 127. Hedaya, E.; Winstein, S. J. Am. Chem. Soc. 1967, 89, 1661. Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363. Ziegler, F. E.; Wester, R. T. Tetrahedron Lett. 1984, 25, 617.
22. 4, and concentrated in vacuo. Purification on silica gel provided compound 6 (178 mg, 0.483 mmol) in 65% overall yield.
23. Methyl ketones are often inert to MCPBA.
24. Compound 16 exists as a 1:1 equilibrium mixture of hemiketal and hydroxyketone in deuteriochloroform.
25. This transformation has been previously realized in modest yields (<40%) by employing monopersulfuric acid [Marker, R. E.; Turner D. L.; Wagner, R. B.; Ulshafer, P. R. J. Am. Chem. Soc. 1941, 63, 772].