Brønsted acid-catalyzed imine amidation

Journal of the American Chemical Society

Volumn 127, Issue 45, 2005, Pages 15696-15697

  Rowland, Gerald B ^a   Zhang, Haile ^a   Rowland, Emily B ^a   Chennamadhavuni, Spandan ^a   Wang, Yong ^a   Antilla, Jon C ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE; ACRYLAMIDE; BENZAMIDE DERIVATIVE; CARBAMIC ACID; CARBOXYLIC ACID; FORMAMIDE; IMINE; PEPTIDE; SULFONAMIDE;

AMIDATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY;

EID: 27844464898     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0533085     Document Type: Article

References (37)

1. For some recent reviews, see: (a) List, B. Tetrahedron 2002, 58, 5573.
2. (b) List, B. Acc. Chem. Res. 2004, 37, 548.
3. (c) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 5248.
4. (d) Dalko, P. I.; Moisan, L. Angew Chem., Int. Ed. 2004, 43, 5138.
5. Recent examples include: (a) McDougal, N. T.; Shaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094.
6. (b) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
7. (c) Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 3418.
8. (d) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804.
9. (e) Momiyama, N.; Yamamoto H. J. Am. Chem. Soc. 2005, 127, 1080.
10. (a) Williams, A. L.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 1612.
11. (b) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204.
12. For leading references, see: (a) Bloch, R. Chem. Rev. 1998, 98, 1407.
13. (b) Comprehensive Asymmetric Catalysis: Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999.
14. (a) Gaunt, M. J.; Spencer, J. B. Org. Lett. 2001, 3, 25.
15. (b) Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319.
16. (c) Wabnitz, T. C.; Spencer, J. B. Org. Lett. 2003, 5, 2141.
17. (d) Wabnitz, T. C.; Yu, J.-Q.; Spencer, J. B. Chem.-Eur. J. 2004, 10, 484.
18. (e) Palomo, C.; Oiarbide, M.; Halder, R.; Kelso, M.; Gomez-Bengoa, E.; Garcia, J. M. J. Am. Chem. Soc. 2004, 126, 9188.
19. (a) Schiff, H. Justus Liebigs Ann. Chem. 1869, 186.
20. (b) Drach, B. S.; Sinitsa, A. D.; Kirsanov, A. V. J. Org. Chem. USSR (English translation) 1969, 5, 2117.
21. (c) Martell, A. E.; Herbst, R. M. J. Org. Chem. 1941, 6, 878.
22. (d) Drach B. S.; Mis'kevich, G. N. J. Org. Chem. USSR (English translation) 1975, 11, 310.
23. (e) Schamp, N. Bull. Soc. Chim. Belg. 1976, 85, 763.
24. (f) Derkach, N. Y.; Garachenkov, G. G.; Slyusarenko, E. I. J. Org. Chem. USSR (English translation) 1982, 18, 60.
25. (g) Mirskova, A. N.; Levkovskaya, G. G.; Bryuzgin, A. A.; Drozdova, T. I.; Kalikhman, I. D.; Voronkov, M. G. J. Org. Chem. USSR (English translation) 1990, 26, 140.
26. Reviews: (a) Goodman. M.; Chorev, M. Acc. Chem. Res. 1979, 12, 1.
27. (b) Chorev, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266.
28. (a) Hernandez, J. F.; Soleihac, J. M.; Roques, B. P.; Fournie-Zaluski, M. C. J. Med. Chem. 1988, 31, 1825.
29. (b) Di Gregorio, G.; Pinori, M.; Verdini, A. S. In Innovation and Perspectives in Solid-Phase Synthesis: Epton, R., Ed.; SPPC (UK) Ltd.: Birmingham. 1992; pp 311-318.
30. (c) Pallai, P. V.; Struthers, R. S.; Goodman, M. Biochemistry 1985, 24, 1933.
31. (d) Nishimura, Y.; Shitara, E.; Adachi, H.; Toyoshima, M.; Nakajima, M.; Okami, Y.; Takeuchi, T. J. Org. Chem. 2000, 65, 2.
32. (e) Fuller, W. D.; Goodman, M.; Verlander, M. S. J. Am. Chem. Soc. 1985, 107, 5821.
33. Katritzky, A. R.; Urogdi, L.; Mayence, A. J. Org. Chem. 1990, 55, 2206.
34. The imines in this report were synthesized according to the procedure in: Wenzel, A.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
35. An excess of inline (2 equiv) was required to minimize side product formation. See Supporting Information for further details. (12) Bao, J.; Wulff, W. D.; Dominy, J. B.; Fumo, M. J.; Grant, E. B.; Rob, A. C.; Whitcomb, M. C.; Yeung, S.-Y.; Ostrander, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 3391
36. In a limited solvent study, it was determined that ether and toluene were optimal for enantioselectivity. Lower ee's were found for THF, acetonitrile, and dichloromethane.
37. Note: For highly reproducible ee's, exhaustively dried catalyst, inline, and sulfonamide are required. See Supporting Information for requisite details.