A convenient one-pot method for the synthesis of N-methoxy-N-methyl amides from carboxylic acids

Bulletin of the Korean Chemical Society

Volumn 31, Issue 1, 2010, Pages 171-173

  Kim, Joong Gon ^a   Jang, Doo Ok ^b  

^a Hanwha Corporation   (South Korea)

^b Yonsei University Wonju   (South Korea)

Author keywords

A amino aeinreb amide; N Methoxy N methyl amide; Trichloroacetonitrile; Triphenylphosphine; Weinreb amide

Indexed keywords

EID: 77951810072     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.01.171     Document Type: Article

References (43)

1. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
2. Balasubramaniam, S.; Aidhen, I. S. Synthesis 2008, 23, 3707.
3. Banwell, M.; Edwards, A.; Smith, J.; Hame, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans 1 2000, 1497.
4. Perez, M.; del Pozo, C.; Reyes, F.; Rodriguez, A.; Francesch, A.; Echavarren, A. M.; Cuevas, C. Angew. Chem., Int. Ed. 2004, 43, 1724.
5. Mulzer, J.; Berger, M. J. Org. Chem. 2004, 69, 891.
6. Zanatta, S. D.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1041.
7. Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Z. Org. Lett. 2003, 5, 925.
8. Evans, D. A.; Connell, B. T. J. Am. Chem. Soc. 2003, 125, 10899.
9. Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. J. Am. Chem. Soc. 2003, 125, 5393.
10. Huckins, J. R.; De Vicente, J.; Rychnovsky, S. D. Org. Lett. 2007, 9, 4757.
11. Gopalarathnam, A.; Nelson, S. G. Org. Lett. 2006, 8, 7.
12. Schuppan, J.; Ziemer, B.; Koert, U. Tetrahedron Lett. 2000, 41, 621.
13. Gomez-Monterrey, I, M.; Campiglia, P. ; Bertamino, A.; Aqui-no, C.; Mazzoni, O.; Diurno, M. V. ; Iacovino, R.; Saviano, M.; Sala, M.; Novellino, E.; Grieco, P. Eur. J.Org. Chem. 2008, 11, 1983.
14. Gomez-Monterrey, I. M.; Campiglia, P.; Bertamino, A.; Mazzoni, O.; Diurno, M. V.; Novellino, E.; Grieco, P. Tetrahedron 2006, 62, 8083.
15. Grieco, P. ; Campiglia, P. ; Gomez-Monterrey, I.; Novel-lino, E. Tetrahedron Lett. 2002, 43, 6297.
16. Wu, Y.; Xu, J.-C. Tetrahedron 2001, 57, 8107.
17. Owens, T. D.; Araldi, G.-L.; Nutt, R. F.; Semple, J. E. Tetrahedron Lett. 2001, 42, 6271.
18. Deagostino, A.; Karini, P. ; Occhiato, E. G.; Pizzuto, L.; Prandi, C.; Venturello, P. J. Org. Chem. 2008, 73, 1941.
19. Martinelli, J. R.; Freckmann, D. M. M.; Buchwald, S. L. Org. Lett. 2006, 8, 4843.
20. Aungst, R. A.; Funk, R. L. J. Am. Chem. Soc. 2001, 123, 9455.
21. Murakami, M.; Hoshino, Y. ; Ito, H.; Ito, Y. Chem. Lett. 1998, 163.
22. Nemoto, H.; Ma, R.; Moriguchi, H.; Kawamura, T.; Kamiya, M.; Shibuya, M. J. Org. Chem. 2007, 72, 9850.
23. Lee, J. I. Bull. Korean Chem. Soc. 2007, 28, 695.
24. Gibson, C. L.; Handa, S. Tetrahedron-Asymmetry 1996, 7, 1281.
25. Braun, M.; Waldmuller, D. Synthesis 1989, 856.
26. Dechantsreiter, M. A.; Burkhart, F.; Kessler, H. Tetrahedron Lett. 1998, 39, 253.
27. Oppolzer, W.; Cunningham, A. F. Tetrahedron Lett. 1986, 27, 5467.
28. Katritzky, A. R.; Yang, H.; Zhang, S.; Wang, M. ARKIVOC 2002, 39.
29. Shreder, K.; Zhang, L.; Goodman, M. Tetrahedron Lett. 1998, 39, 221.
30. Maugras, I.; Poncet, J.; Jouin, P. Tetrahedron 1990, 46, 2807.
31. De Luca, L.; Gaicomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534.
32. Lee, J. I.; Park, H. Bull. Korean. Chem. Soc. 2001, 22, 421.
33. Sibi, M. P.; Stressman, C. C.; Schultz, J. A.; Christensen, J. W.; Lu, J.; Marvin, M. Synth. Commun. 1995, 25, 1255.
34. White, J. M.; Tunoori, A. R.; Turunen, B. J.; Georg, G. I. J. Org. Chem. 2008, 73, 1941.
35. Tunoori, A. R.; White, J. M.; Georg, G. I. Org. Lett. 2000, 2, 4091.
36. Han, K.-D.; Kim, M. Lett. Org. Chem. 2007, 4, 20.
37. Woo, J. C. S.; Fenster, E. Dake, G. R. J. Org. Chem. 2004, 69, 8984.
38. Kim, M.; Lee, H.; Han, K.-J.; Kay, K.-Y. Synth. Commun. 2003, 33, 4013.
39. Davies, D. T.; O'Hanlon, P. J. Synth. Commun. 1988, 18, 2273.
40. Jang, D. O.; Park, D. J.; Kim, J. Tetrahedron Lett. 1999, 40, 5323.
41. D = -10.2 (c = 1.0, MeOH)) Diacel Chiralcel OC; n-hexane/IPA (90/10, v/v); flow rate = 1.0 mL/min ; UV (λ = 254 nm); retention time for L-form = 7.8 min; retention time for D-form = 9.5 min.
42. Bailén, M. A.; Chinchilla, R; Dodsworth, D. J.; and Nájera, C. Tetrahedron Lett. 2001, 42, 5013.
43. Sureshbabu, V. V.; Hemantha, H. P. ARKIVOC 2008, 243.