1-Benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-ones: Mosher-Bt reagents

Journal of Organic Chemistry

Volumn 72, Issue 11, 2007, Pages 4268-4271

  Katritzky, Alan R ^a   Mohapatra, Prabhu P ^a   Fedoseyenko, Dmytro ^a   Duncton, Matthew ^b   Steel, Peter J ^c  

^a University of Florida   (United States)

^b EVOTEC AG   (Germany)

^c UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTRIAZOLE; QUANTITATIVE YIELDS; REAGENTS;

ACETONITRILE; AMIDES; AMINO ACIDS; DERIVATIVES; PEPTIDES; WATER;

ALCOHOLS;

1 BENZOTRIAZOL 1 YL 3,3,3 TRIFLUORO 2 METHOXY 2 PHENYLPROPAN 1 ONE; ACETONE; ACETONITRILE; AMIDE; AMINO ACID DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; PEPTIDE DERIVATIVE; PHENYLPROPIONIC ACID DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SOLUBILITY; STRUCTURE ANALYSIS;

EID: 34249810946     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070278a     Document Type: Article

References (48)

1. Katritzky, A. R.; Suzuki, K.; Wang, Z. Synlett 2005, 1656.
2. (a) Katritzky, A. R.; Zhang, Y.; Singh, S. K. Synthesis 2003, 2795.
3. (b) Katritzky, A. R.; Meher, N. K.; Cai, C.; Singh, S. K. Rev. Soc. Quim. Mex. 2004, 48, 275.
4. Katritzky, A. R.; He, H.-Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210.
5. Katritzky, A. R.; Yang, H.; Zhang, S.; Wang, M. ARKIVOC 2002, xi, 39.
6. Katritzky, A. R.; Pastor, A.; Voronkov, M. V. J. Heterocycl. Chem. 1999, 36, 777.
7. (a) Katritzky, A. R.; Pastor, A. J. Org. Chem. 2000, 65, 3679.
8. (b) Katritzky, A. R.; Jiang, R.; Suzuki, K. J. Org. Chem. 2005, 70, 4993.
9. (c) Katritzky, A. R.; Meher, N. K.; Singh, S. K. J. Org. Chem. 2005, 70, 7792.
10. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Wang, M. J. Org. Chem. 2003, 68, 1443.
11. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Wang, M. J. Org. Chem. 2003, 68, 4932.
12. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Akhmedova, R. G. ARKIVOC 2005, vi, 329.
13. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Gromova, A. V.; Witek, R.; Steel, P. J. J. Org. Chem. 2005, 70, 9211.
14. Caprio, V. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier: New York, 2005; p 135.
15. (a) Katritzky, A. R.; Suzuki, K.; Singh, S. K. Synthesis 2004, 2645.
16. (b) Katritzky, A. R.; Angrish, P.; Hür, D.; Suzuki, K. Synthesis 2005, 398.
17. (c) Katritzky, A. R.; Angrish, P.; Suzuki, K. Synthesis 2006, 411.
18. (d) Katritzky, A. R.; Todadze, E.; Cusido, J.; Angrish, P.; Shestopalov, A. A. Chem. Biol. Drug Des. 2006, 68, 37.
19. (e) Katritzky, A. R.; Todadze, E.; Shestopalov, A. A.; Cusido, J.; Angrish, P. Chem. Biol. Drug Des. 2006, 68, 42.
20. (f) Katritzky, Alan, R.; Meher, G.; Angrish, P. Chem. Biol. Drug Des. 2006, 68, 326.
21. Katritzky, A. R.; Singh, S. K.; Cai, C.; Bobrov, S. J. Org. Chem. 2006, 71, 3364.
22. Katritzky, A. R.; Angrish, P. Steroids 2006, 71, 660.
23. Katritzky, A. R.; Singh, S. K.; Akhmedova, R.; Cai, C.; Bobrov, S. ARKIVOC 2007, vi, 6.
24. (a) Katritzky, A. R.; Le, K. N. B.; Khelashvili, L.; Mohapatra, P. P. J. Org. Chem. 2006, 71, 9861.
25. (b) Katritzky, A. R.; Angrish, P. Synthesis 2006, 4135.
26. (a) Kusumi, T.; Ooi, T.; Ohkubo, Y.; Yabuuchi, T. Bull. Chem. Soc. Jpn. 2006, 79, 965.
27. (b) Furusawa, M.; Hashimoto, T.; Noma, Y.; Asakawa, Y. Chem. Pharm. Bull. 2006, 54, 996.
28. (c) Barreiros, M. L.; David, J. M.; David, J. P. Quim. Nova 2005, 28, 1061.
29. (d) Seco, J. M.; Quiñoá, E.; Riguera, R. Chem. Rev. 2004, 104, 17.
30. (e) Omata, K.; Fujiwara, T.; Kabuto, K. Tetrahedron: Asymmetry 2002, 13, 1655.
31. (f) Kubota, T.; Tsuda, M.; Kobayashi, J. Org. Lett. 2001, 3, 1363.
32. (g) Morohashi, A.; Satake, M.; Nagai, H.; Oshima, Y.; Yasumoto, T. Tetrahedron 2000, 56, 8995.
33. (h) Chang, L. C.; Chavez, D.; Song, L. L.; Farnsworth, N. R.; Pezzutto, J. M.; Kinghorn, A. D. Org. Lett. 2000, 2, 515.
34. (i) Murata, M.; Matsuoka, S.; Matsumori, N.; Paul, G. K.; Tachibana, K. J. Am. Chem. Soc. 1999, 121, 870.
35. (j) Rossouw, W.; Hundt, A. F.; Steenkamp, J. A.; Ferreira, D. Tetrahedron 1994, 50, 12477.
36. (k) Rieser, M. J.; Hui, Y.; Rupprecht, J. K.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hanson, P. R.; Zhuang, Z.; Hoye, T. R. J. Am. Chem. Soc. 1992, 114, 10203.
37. (l) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
38. (m) Ward, D. E.; Rhee, C. K. Tetrahedron Lett. 1991, 32, 7165.
39. (n) Ohtani, I.; Kusumi, T.; Ishitsuka, M. O.; Kakisawa, H. Tetrahedron Lett. 1989, 30, 3147.
40. (o) Kusumi, T.; Ohtani, I.; Inouye, Y.; Kakisawe, H. Tetrahedron Lett. 1988, 29, 4731.
41. (p) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
42. (q) Yasuhara, F.; Yamaguchi, S.; Kasai, R.; Tanaka, D. Tetrahedron Lett. 1986, 27, 4033.
43. (r) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
44. (s) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143.
45. (t) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
46. (u) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1968, 90, 3732.
47. Although derivatization of an alcohol (or amine) with (R)-MTPA acid gives the corresponding (R)-MTPA ester (or amide), the widely used (R)-MTPA acid chloride gives the corresponding (S)-MTPA ester (or amide), (a) Joshi, B. S.; Pelletier, S. W. Heterocycles 1999, 51, 183.
48. (b) Joshi, B. S.; Newton, M. G.; Lee, D. W.; Barber, A. D.; Pelletier, S. W. Tetrahedron: Asymmetry 1996, 7, 25.