Tandem oxidation processes for the preparation of functionalized cyclopropanes

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3997-4000

  Oswald, Magalie F ^a   Raw, Steven A ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOPROPANE DERIVATIVE; LIGNAN DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL REACTION; METHODOLOGY; MOLECULAR PROBE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 8744223189     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0483394     Document Type: Article

References (32)

1. For examples, see: (a) Raw, S. A.; Reid, M.; Roman, E.; Taylor, R. J. K. Synlett 2004, 819. (b) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Org. Biomol. Chem. 2004, 2, 788. (c) Blackburn, L.; Taylor, R. J. K. Org. Lett. 2001, 3, 1637. (d) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616 and references therein.
2. For examples, see: (a) Raw, S. A.; Reid, M.; Roman, E.; Taylor, R. J. K. Synlett 2004, 819. (b) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Org. Biomol. Chem. 2004, 2, 788. (c) Blackburn, L.; Taylor, R. J. K. Org. Lett. 2001, 3, 1637. (d) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616 and references therein.
3. For examples, see: (a) Raw, S. A.; Reid, M.; Roman, E.; Taylor, R. J. K. Synlett 2004, 819. (b) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Org. Biomol. Chem. 2004, 2, 788. (c) Blackburn, L.; Taylor, R. J. K. Org. Lett. 2001, 3, 1637. (d) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616 and references therein.
4. For examples, see: (a) Raw, S. A.; Reid, M.; Roman, E.; Taylor, R. J. K. Synlett 2004, 819. (b) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Org. Biomol. Chem. 2004, 2, 788. (c) Blackburn, L.; Taylor, R. J. K. Org. Lett. 2001, 3, 1637. (d) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616 and references therein.
5. (a) Ningsanont, N.; Black, D. S. C.; Chanpen, R.; Thebtaranonth, Y. J. Med. Chem. 2003, 46, 2397.
6. (b) Wipf, P.; Reeves, J. T.; Balachandran, R.; Day, B. W. J. Med. Chem. 2002, 45, 1901.
7. (c) Rugutt, J. K.; Henry, C. W.; Franzblau, S. G.; Warner, I. M. J. Agric. Food Chem. 1999, 47, 3402.
8. (d) Han, S.-Y.; Cho, S.-H.; Kim, S.-Y.; Seo, J.-T.; Moon, S.-J.; Jhon, G.-L. Bioorg. Med. Chem. Lett. 1999, 9, 59.
9. (e) Barrett, A. G. M.; Doubleday, W. W.; Hamprecht, D.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Chem. Commun. 1997, 1693.
10. (f) Bucsh, R. A.; Domagala, J. M.; Laborde, E.; Sesnie, J. C. J. Med. Chem. 1993, 36, 4139.
11. (g) Martinez, G. R.; Walker, K. A. M.; Hirschfeld, D. R.; Maloney, P. J.; Yang, D. S.; Rosenkranz, R. P. J. Med. Chem. 1989, 32, 890.
12. (a) For a comprehensive summary, see: Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; Chapter 4, p 71.
13. (b) Helquist, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, Chapter 4.6, p 951.
14. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424.
15. (d) Payne, G. B. J. Org. Chem. 1967, 32, 3351.
16. (e) Quintana, J.; Torres, M.; Serratosa, F. Tetrahedron 1973, 29, 2065.
17. 2. Concentration of the combined organics in vacuo followed by flash column chromatography on silica gave the desired product. For more specific procedures, see the Supporting Information.
18. All known compounds gave satisfactory data (see ref 4); all novel compounds were fully characterized by spectroscopic methods and HRMS.
19. (a) Boland, W.; Niedermeyer, U. Synthesis 1987, 28.
20. (b) Wu, P.-L.: Wang, W.-S. J. Org. Chem. 1994, 59, 622.
21. (c) Curley, R. W., Jr.; DeLuca, H. F. J. Org. Chem. 1984, 49, 1944.
22. (d) Hammerschmidt, F.; Zbiral, E. Liebigs Ann. Chem. 1977, 1026.
23. (e) Doyle, M. P.; Dorow, R. L.; Tamblyn, W. H. J. Org. Chem. 1982, 47, 4059.
24. (f) Duhamel, P.; Poirier, J.-M.; Hennequin, L. Tetrahedron Lett. 1984, 25, 1471.
25. (g) Aggarwal, V. K.; Smith, H. W.; Hynd, G.; Jones, R. V. H.; Fieldhouse, R.; Spey, S. E. J. Chem. Soc., Perkin Trans. 1 2000, 3267. For the methyl ester analogue: Adams, J.; Hoffman, L., Jr.; Trost, B. M. J. Org. Chem. 1970, 35, 1600.
26. (g) Aggarwal, V. K.; Smith, H. W.; Hynd, G.; Jones, R. V. H.; Fieldhouse, R.; Spey, S. E. J. Chem. Soc., Perkin Trans. 1 2000, 3267. For the methyl ester analogue: Adams, J.; Hoffman, L., Jr.; Trost, B. M. J. Org. Chem. 1970, 35, 1600.
27. (h) Matano, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2703
28. (i) Rai, K. M. L.; Anjanamurthy, C.; Radhakrisan, P. M. Synth. Commun. 1990, 9, 1273.
29. For examples, see; Hantawong, K.; Murphy, W. S. J. Chem. Res., Miniprint 1988, 2520 (b) Murphy, W. S.; Wattanasin, S. J. Chem. Soc., Perkin Trans. 1 1982, 1029.
30. For examples, see; Hantawong, K.; Murphy, W. S. J. Chem. Res., Miniprint 1988, 2520 (b) Murphy, W. S.; Wattanasin, S. J. Chem. Soc., Perkin Trans. 1 1982, 1029.
31. 2 (10.0 equiv). The mixture was heated to reflux and stirred until complete reaction was observed by TLC. The mixture was then filtered through Celite and the residue washed with solvent. Concentration in vacuo followed by flash column chromatography on silica gave the desired product. For more specific procedures, see the Supporting Information.
32. Murphy, W. S.; Wattanasin, S. J. Chem. Soc., Perkin Trans. 1 1982, 271.