A new β-keto amide synthesis

Synthesis

Volumn , Issue 15, 2002, Pages 2191-2194

  Chen, Yanping ^a   Sieburth, Scott McN ^b  

^a STONY BROOK UNIVERSITY   (United States)

^b Temple University   (United States)

Author keywords

Amides; Carboxylic acids; Condensation; Ketones; Nitriles

Indexed keywords

ACETIC ACID; CONDENSATION; ESTERS;

DECARBOXYLATION;

SYNTHESIS (CHEMICAL);

AMIDE; CARBOXYLIC ACID; KETONE; MALONIC ACID; NITRILE; PROPIONIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0036416729     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34845     Document Type: Article

References (51)

1. (a) Claisen, L.; Meyer, K. Chem. Ber. 1902, 30, 583.
2. (b) Moureu, C.; Lazennec, I. Bull. Soc. Chim. Fr. 1908, 1066.
3. Sung, K.; Wu, S.-Y. Synth. Commun. 2001, 31, 3069.
4. Schroth, W.; Spitzner, R.; Hugo, S. Synthesis 1982, 199.
5. Dekhane, M.; Douglas, K.T.; Gilbert, P. Tetrahedron Lett. 1996, 37, 1883.
6. Sørensen, U.S.; Falch, E.; Krogsgaard-Larsen, P. J. Org. Chem. 2000, 65, 1003.
7. Witzeman, J.S.; Nottingham, W.D.J. Org. Chem. 1991, 56, 1713.
8. (a) Cossy, J.; Theilend, A. Synthesis 1989, 753.
9. (b) Hoffman, R.V.; Huizenga, D.J.J. Org. Chem. 1991, 56, 6435.
10. Kumar, P.; Pandey, R.K. Synlett 2000, 251.
11. Garcia, M.J.; Rebolledo, F.; Gotor, V. Tetrahedron 1994, 50, 6935.
12. Kim, H.-O.; Olsen, R.K.; Choi, O.-S.J. Org. Chem. 1987, 52, 4531.
13. (a) Gramain, J.C.; Remuson, R.; Vallee, D.J. Org. Chem. 1985, 50, 710.
14. (b) Kuzma, P.C.; Brown, L.E.; Harris, T.M.J. Org. Chem. 1984, 49, 2015.
15. (c) McWhorter, W.; Fredenhagen, A.; Nakanishi, K.; Komura, H.J. Chem. Soc., Chem. Commun. 1989, 299.
16. (d) Morris, J.; Wishka, D.G.; Fang, Y. Synth. Commun. 1994, 24, 849.
17. (a) Hendi, S.B.; Hendi, M.S.; Wolfe, J.F. Synth. Commun. 1987, 17, 13.
18. (b) Lasley, L. C.; Wright, B. B. Synth. Commun. 1989, 19, 59.
19. Ferri, R. A.; Pitacco, G.; Valentin, E. Tetrahedron 1978, 34, 2537.
20. Armati, A.; De Ruggieri, P.; Rossi, E.; Stradi, R. Synthesis 1986, 573.
21. Pak, C. S.; Yang, H. C.; Choi, E. B. Synthesis 1992, 1213.
22. Hiyamizu, H.; Ooi, H.; Inomoto, Y.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2001, 3, 473.
23. (a) Sato, M.; Ogasawara, H.; Komatsu, S.; Kato, T. Chem. Pharm. Bull. 1984, 32, 3848.
24. (b) Clemens, R. J.; Hyatt, J. A. J. Org. Chem. 1985, 50, 2431.
25. Cossy, J.; Belotti, D.; Thellend, A.; Pete, J. P. Synthesis 1988, 720.
26. DeShong, P.; Cipollina, J. A.; Lowmaster, N. K. J. Org. Chem. 1988, 53, 1356.
27. Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481.
28. Rao, A. V. R.; Chakraborty, T. K.; Reddy, K. L. Tetrahedron Lett. 1990, 31, 1439.
29. (a) Wierenga, W.; Skulnick, H. I. J. Org. Chem. 1979, 44, 310.
30. (b) Wierenga, W.; Skulnick, H. J. Org. Synth., Coll. Vol. VII 1990, 213.
31. Ireland, R. E.; Marshall, J. A. J. Am. Chem. Soc. 1959, 81, 2907.
32. Neukom, C.; Richardson, D. P.; Myerson, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1986, 108, 5559.
33. (a) Ader, T. A.; Champey, C. A.; Kuznetsova, L. V.; Li, T.; Lim, Y.-H.; Rucando, D.; Sieburth, S. McN. Org. Lett. 2001, 3, 2165.
34. (b) Sieburth, S. McN.; McGee, K. F. Jr.; Zhang, F.; Chen, Y. J. Org. Chem. 2000, 65, 1972.
35. Gellman, S. H.; Dado, G. P.; Liang, G. B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164.
36. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
37. (a) Elnagdi, M. H.; Elmoghayar, M. R. H.; Elgemeie, G. E. H. Synthesis 1984, 1.
38. (b) Tsunoda, T.; Takagi, H.; Takaba, D.; Kaku, H.; Itô, S. Tetrahedron Lett. 2000, 41, 235.
39. (c) Fleming, F. F.; Guo, J.; Wang, Q.; Weaver, D. J. Org. Chem. 1999, 64, 8568.
40. (d) Fleming, F. F.; Huang, A.; Sharief, V. A.; Pu, Y. J. Org. Chem. 1997, 62, 3036.
41. (e) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356.
42. (f) AlHusaini, A. H.; Muqtar, M.; Ali, S. A. Tetrahedron 1991, 47, 7719.
43. Kirsten, C. N.; Schrader, T. H. J. Am. Chem. Soc. 1997, 119, 12061.
44. Sim, M. M.; Lee, C. L.; Ganesan, A. Tetrahedron Lett. 1998, 39, 2195.
45. (a) Sim, M. M.; Lee, C. L.; Ganesan, A. Tetrahedron Lett. 1998, 39, 6399.
46. (b) Goasdoue, C.; Couffignal, R. Tetrahedron Lett. 1979, 1585.
47. 16
48. Rigo, B.; Fasseur, D.; Cauliez, P.; Couturier, D. Tetrahedron Lett. 1989, 30, 3073.
49. McFadden, H. G.; Huppatz, J. L. Aust. J. Chem, 1991, 44, 1263.
50. Foehlisch, B.; Herter, R.; Wolf, E.; Stezowski, J. J.; Eckle, E. Chem. Ber. 1982, 115, 355.
51. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1966, 1518.