Esters and amides from activated alcohols using manganese(IV) dioxide: Tandem oxidation processes

Synthesis

Volumn , Issue 7, 2003, Pages 1055-1064

  Foot, Jonathan S ^a   Kanno, Hisashi ^a   Giblin, Gerard M P ^b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Alcohols; Amides; Esters; Oxidations; Tandem reactions

Indexed keywords

AMMONIA; ESTERS; MANGANESE COMPOUNDS; OXIDATION;

CHEMICAL CONVERSION PROCESSES;

METHANOL;

ALCOHOL; AMIDE; AMMONIA; ESTER; MANGANESE DIOXIDE; METHANOL; METHYL GROUP; SODIUM CYANIDE;

ARTICLE; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0038018728     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39163     Document Type: Article

References (55)

1. For activated alcohols see: (a) Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815. (b) Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337. (c) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616. (d) Runcie, K. A.; Taylor, R. J. K. Chem. Commun. 2002, 9, 974. (e) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115. (f) For non-activated alcohols, see: Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215.
2. For activated alcohols see: (a) Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815. (b) Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337. (c) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616. (d) Runcie, K. A.; Taylor, R. J. K. Chem. Commun. 2002, 9, 974. (e) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115. (f) For non-activated alcohols, see: Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215.
3. For activated alcohols see: (a) Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815. (b) Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337. (c) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616. (d) Runcie, K. A.; Taylor, R. J. K. Chem. Commun. 2002, 9, 974. (e) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115. (f) For non-activated alcohols, see: Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215.
4. For activated alcohols see: (a) Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815. (b) Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337. (c) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616. (d) Runcie, K. A.; Taylor, R. J. K. Chem. Commun. 2002, 9, 974. (e) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115. (f) For non-activated alcohols, see: Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215.
5. For activated alcohols see: (a) Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815. (b) Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337. (c) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616. (d) Runcie, K. A.; Taylor, R. J. K. Chem. Commun. 2002, 9, 974. (e) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115. (f) For non-activated alcohols, see: Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215.
6. For activated alcohols see: (a) Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815. (b) Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337. (c) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616. (d) Runcie, K. A.; Taylor, R. J. K. Chem. Commun. 2002, 9, 974. (e) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115. (f) For non-activated alcohols, see: Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215.
7. (a) Blackburn, L.; Taylor, R. J. K. Org. Lett. 2001, 3, 1637.
8. (b) Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 7337.
9. Kanno, H.; Taylor, R. J. K. Synlett 2002, 1287.
10. McAllister, G. D.; Wilfred, C. D.; Taylor, R. J. K. Synlett 2002, 1291.
11. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616.
12. Gilman, N. W. J. Chem. Soc., Chem. Commun. 1971, 733.
13. Foot, J. S.; Kanno, H.; Giblin, G. M. P.; Taylor, R. J. K. Synlett 2002, 1293.
14. (a) For a mechanistic explanation, see: Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241.
15. (b) For recent use in synthesis, see: Ragharan, S.; Anuradha, K. Tetrahedron Lett. 2002, 43, 5181.
16. Papaioannou, D.; Francis, G. W.; Aksnes, D. W.; Maartmann-Moe, K.; Brekke, T. Acta Chem. Scand. 1990, 44, 90.
17. Holland, H. L.; Kindermann, M.; Kumaresan, S.; Stefanac, T. Tetrahedron: Asymmetry 1993, 4, 1353.
18. Noureldin, N. A.; Zhao, D.; Lee, D. G. J. Org. Chem. 1997, 62, 8767.
19. Hans, J. J.; Driver, R. W.; Burke, S. D. J. Org. Chem. 2000, 65, 2114.
20. Bauer, R.; Remiger, P.; Wagner, H. Phytochemistry 1989, 28, 505.
21. Dietz, B.; Bauer, R. Pharm. Biol. 2001, 39, 11.
22. Stöhr, J. R.; Xiao, P. G.; Bauer, R. Planta Med. 1999, 65, 175.
23. 2,4-Dodecadien-1-o1 purchased from Fluka, cat. no. 00554.
24. Keck, G. E.; McLaws, M. D.; Wager, T. T. Tetrahedron 2000, 56, 9875.
25. Patil, V. J.; Maevers, U. Tetrahedron Lett. 1996, 37, 1281.
26. Nilsson, K.; Ullenius, C.; Krause, N. J. Am. Chem. Soc. 1996, 118, 4194.
27. Avila-Zarraga, J. G.; Martinez, R. Synth. Commun. 2001, 31, 2177.
28. Kuhn, G. J. Am. Chem. Soc. 1948, 70, 3370.
29. Lai, G.; Anderson, W. K. Synth. Commun. 1997, 27, 1281.
30. Thiele, R. Justus Liebigs Ann. Chem. 1899, 306, 215.
31. Rhee, H.; Kim, J. Y. Tetrahedron Lett. 1998, 39, 1365.
32. Hecht, K. Tetrahedron Lett. 1973, 1397.
33. Batori, S.; Doepp, D.; Messmer, A. Tetrahedron 1994, 50, 4699.
34. Krapcho, A. P.; Waterhouse, D. J.; Hammach, A.; Domenico, R.; Menta, E. Synth. Commun. 1997, 27, 781.
35. Anderson, B. J. Am. Chem. Soc. 1958, 80, 992.
36. Moulines, F.; Ruiz, J.; Astruc, D. J. Organomet. Chem. 1988, 340, C13.
37. Qian, C.; Wang, L. Tetrahedron 2000, 51, 7193.
38. Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546.
39. Gajida, T.; Zwierzak, B. Synthesis 1981, 1005.
40. Anker, L.; Lauterwein, J.; van de Waterbeemd, H.; Testa, B. Helv. Chim. Acta 1984, 67, 706.
41. Abramovitch, R. A.; Alvernhe, G.; Bartnik, R.; Dassanayake, N. L.; Inbasekaran, M. N.; Kato, S. J. Am. Chem. Soc. 1981, 103, 4558.
42. Whitehouse, D. L.; Nelson, K. H.; Savinov, S. N.; Löwe, R. S.; Austin, D. J. Bioorg. Med. Chem. 1998, 6, 1273.
43. Huisgen, R.; Remlinger, H. Justus Liebigs Ann. Chem. 1956, 599, 177.
44. Auzeil, N.; Largeron, M.; Fleury, M. J. Chem. Soc., Perkin Trans. 2 1999, 1703.
45. Carloni, P.; Eberson, L.; Greci, L.; Sgarabotto, P.; Stipa, P. J. Chem. Soc., Perkin Trans. 2 1996, 1297.
46. Padwa, A.; Austin, D. J.; Price, A. T.; Weingarten, M. D. Tetrahedron 1996, 52, 3247.
47. Suezawa, H.; Tsuchiya, K.; Tahara, E.; Hirota, M. Bull. Chem. Soc. Jpn. 1987, 60, 3973.
48. Alonso, E.; Ramon, D. J.; Yus, M. Tetrahedron 1998, 54, 13629.
49. Lluch, A.-M.; Gibert, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron 1996, 52, 3973.
50. Agwanda, V. C. J. Chem. Eng. Data 1984, 29, 235.
51. Herbst, R. M.; Roberts, C. W.; Givens, H. T. F.; Harvill, E. K. J. Org. Chem. 1952, 17, 262.
52. Huang, Z.; Wen, L.; Huang, X. Synth. Comm. 1990, 20, 2579.
53. Hoberg, H.; Riegel, H. J. J. Organomet. Chem. 1983, 241, 245.
54. Degani, I.; Dughera, S.; Fochi, R.; Serra, E. Synthesis 1999, 1200.
55. Abarbri, M.; Parrain, J. L.; Duchêne, A. Synth. Commun. 1998, 28, 239.