Directed dihydroxylation of allylic trichloroacetamides

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 2980-2981

  Donohoe, Timothy J ^a   Blades, Kevin ^a   Helliwell, Madeleine ^a   Moore, Peter R ^a   Winter, Jonathan J G ^a   Stemp, Geoffrey ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROACETAMIDE;

ARTICLE; CHEMICAL REACTION; HYDROGEN BOND; HYDROXYLATION; OXIDATION; RELIABILITY; SYNTHESIS;

EID: 0033617137     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982468e     Document Type: Article

References (31)

1. For general reviews, see: (a) Schroeder, M. Chem. Rev. 1980, 80, 187. (b) Lohray, B. B. Tetrahedron: Asymmetry 1992, 3, 1317. (c) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
2. For general reviews, see: (a) Schroeder, M. Chem. Rev. 1980, 80, 187. (b) Lohray, B. B. Tetrahedron: Asymmetry 1992, 3, 1317. (c) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
3. For general reviews, see: (a) Schroeder, M. Chem. Rev. 1980, 80, 187. (b) Lohray, B. B. Tetrahedron: Asymmetry 1992, 3, 1317. (c) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
4. (a) Cha, J. K.; Christ W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
5. (b) Cha, J. K.; Christ W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947.
6. (c) Cha, J. K.; Christ W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247.
7. (d) Cha, J. K.; No-Soo Kin. Chem. Rev. 1996, 95, 1761.
8. See ref 2d. For recent examples, see: (a) Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625. (b) Dee, M. F.; Rosati, R. L. Bioorg. Med. Chem. Lett. 1995, 5, 949. (c) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293.
9. See ref 2d. For recent examples, see: (a) Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625. (b) Dee, M. F.; Rosati, R. L. Bioorg. Med. Chem. Lett. 1995, 5, 949. (c) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293.
10. See ref 2d. For recent examples, see: (a) Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625. (b) Dee, M. F.; Rosati, R. L. Bioorg. Med. Chem. Lett. 1995, 5, 949. (c) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293.
11. See: (a) Kiso, M.; Kobayashi, T.; Hasegawa, A. Agric. Biol. Chem. 1980, 44, 169. (b) Danishefsky, S.; Lee, J.-Y. J. Am. Chem. Soc. 1989, 111, 4829.
12. See: (a) Kiso, M.; Kobayashi, T.; Hasegawa, A. Agric. Biol. Chem. 1980, 44, 169. (b) Danishefsky, S.; Lee, J.-Y. J. Am. Chem. Soc. 1989, 111, 4829.
13. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.
14. Donohoe, T. J.; Moore, P. R.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1997, 38, 5027.
15. (a) Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
16. (b) Overman, L. E. Acc. Chem. Res. 1980, 13, 218.
17. (c) Overman, L. E.; Clizbe, L. A.; Freerks, R. L.; Marlowe, C. K. J. Am. Chem. Soc. 1981, 103, 2807.
18. (d) Nishikawa, T.; Asai, M.; Ohyabu N.; Isobe, M. J. Org. Chem. 1998, 63, 188.
19. tOCONHR) and found to be less effective hydrogen-bond donors.
20. 3COOH (cat.): yields were 80-90%.
21. All new compounds were fully characterized. Full details of the X-ray structures of syn-6 (acetonide), syn-8, syn-10, and anti-14 (acetonide) will be published in a full account of this work.
22. Corey, E. J.; Sarshar, S.; Azimiora, M. D.; Newbold R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851.
23. (a) Donohoe, T. J.; Garg, R.; Moore, P. R. Tetrahedron Lett. 1996, 37, 3407.
24. (b) Donohoe, T. J.; Moore, P. R.; Beddoes, R. L. J. Chem. Soc., Perkin Trans. 1 1997, 43.
25. (c) Donohoe, T. J.; Blades, K.; Helliwell, M.; Waring, M. J.; Newcombe, N. J.Tetrahedron Lett. 1998, 39, 8755.
26. (a) Daluge, S.; Vince, R. J. Org. Chem, 1978, 43, 2311.
27. (b) Csuk, R.; Dörr, P. Tetrahedron: Asymmetry 1994, 5, 269.
28. Poli, G. Tetrahedron Lett. 1989, 30, 7385. See also: Ward, S. E.; Holmes, A. B.; McCague, R. Chem. Commun. 1997, 2085.
29. Poli, G. Tetrahedron Lett. 1989, 30, 7385. See also: Ward, S. E.; Holmes, A. B.; McCague, R. Chem. Commun. 1997, 2085.
30. (a) Tomioka, K.; Nakajima, M.; Iitaka, Y.; Koga, K. Tetrahedron Lett. 1988, 29, 573.
31. (b) Hanessian, S.; Meffre, P.; Girard, M.; Beaudoin, S.; Sancéau, J.-Y.; Bennani, Y. J. Org. Chem. 1993, 58, 1991.