Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8739-8741

  Hanselmann, Roger ^a,b   Zhou, Jiacheng ^a,b   Ma, Philip ^a,c   Confalone, Pat N ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b Rib X Pharmaceuticals   (United States)

^c Synica USA Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHELATION; DERIVATIVES; SYNTHESIS (CHEMICAL);

CYCLOADDITION REACTIONS;

AMINO ACIDS;

ACYCLIC BETA AMINO ACID; ALCOHOL; AMINE; AMINO ACID; BETA AMINO ACID; BROMINE DERIVATIVE; CARBOXYLIC ACID; CHELATING AGENT; CYCLIC BETA AMINO ACID; DRUG DERIVATIVE; GLYCINE; ISOXAZOLE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; MAGNESIUM DIBROMIDE; N HYDROXYPHENYLGLYCINOL; N-PHENYLGLYCINE; NITROGEN OXIDE; NITRONES; PHENYLGLYCINE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CHELATION; CHEMISTRY; CHIRALITY; CYCLIZATION; CYCLOADDITION; DIASTEREOISOMER; STEREOISOMERISM; SYNTHESIS;

ACIDS, ACYCLIC; AMINES; AMINO ACIDS; CATALYSIS; CHELATING AGENTS; CYCLIZATION; GLYCINE; ISOXAZOLES; NITROGEN OXIDES; STEREOISOMERISM;

EID: 0142196815     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034940o     Document Type: Article

References (50)

1. Recent reviews: (a) Karlsson, S.; Högberg, H. Org. Prep. Proced. Int. 2001, 33, 103-172.
2. (b) Zecchi, G.; Broggini, G. Synthesis 1999, 905-917.
3. (c) Jørgensen, K. A.; Gothelf, K. V. Chem. Rev. 1998, 98, 863-909.
4. (d) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol.4, 1069-1109.
5. (e) Wade, P. A. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford, 1991; Vol.4, 1111-1168.
6. (a) Ding, X.; Taniguchi, K.; Ukaji, Y.; Inomata, K. Chem. Lett. 2001, 468-469.
7. (b) Gothelf, K. V.; Jorgensen, K. A. Chem. Commun. 2000, 1449-1458.
8. (c) Jen, W. S.; Wiener, J. J. M.; McMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874-9875.
9. (a) Long, A.; Baldwin, S. W. Tetrahedron Lett. 2001, 42, 5343-5345.
10. (b) Tamura, O.; Gotanda, K.; Yoshino, J.; Morita, Y.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Mita, N.; Yamashita, M.; Ishibashi, H.; Sakamoto M. J. Org. Chem. 2000, 65, 8544-8551.
11. (c) Tamura, O.; Mita, N.; Kusaka, N.; Suzuki, H.; Sakamato, M. Tetrahedron Lett. 1997, 38, 429-432.
12. (d) Huber, R.; Vasella, A. Tetrahedron 1990, 46, 33-58.
13. (a) Ina, H.; Ito, M.; Kibayashi, C. J. Org. Chem. 1996, 61, 1023-1029.
14. (b) Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett 1993, 395-396.
15. (c) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329-9350.
16. For applications of N-hydroxy-α-methylbenzylamine in natural product syntheses: (a) Beccalli, E. M.; Broggini, G.; La Rosa, C.; Passarella, D.; Pilati, T.; Terraneo, A.; Zecchi, G. J. Org. Chem. 2000, 65, 8924-8932.
17. (b) Arnone, A.; Broggini, G.; Passarella, D.; Terraneo, A.; Zecchi, G. J. Org. Chem. 1998, 63, 9279-9284.
18. (c) Xu, Z.; Johannes, C. W.; La, D. S.; Hofilena, G. E.; Hoveyda, A. H. Tetrahedron 1997, 53, 16377-16390.
19. (d) Baldwin, S. W.; Aubé, J.; McPhail, A. T. J. Org. Chem. 1991, 56, 6546-6550.
20. (e) Keirs, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. 1, 1991, 1041-1051.
21. (f) Keirs, D.; Moffat, D.; Overton, K. J. Chem. Soc., Chem. Commun. 1988, 654-655.
22. (g) Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron 1985, 41, 3455-3462.
23. (h) Kametani, T.; Nagahara, T.; Honda, T. J. Org. Chem. 1985, 50, 2327-2331.
24. (i) Wovkulich, P. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1981, 103, 3956-3958.
25. (j) Tice, C. M.; Ganem, B. J. Org. Chem. 1983, 48, 5048-5050.
26. (a) Broggini, G.; Folcio, F.; Sardone, N.; Zecchi, G. Tetrahedron Lett. 1996, 52, 11849-11856.
27. (b) Baldwin, S. W.; McFadyen, R. B.; Aubé, J.; Wilson, J. D. Tetrahedron Lett. 1991, 32, 4431-4434.
28. (c) Belzecki, C.; Panfil, I. J. Org. Chem. 1979, 44, 1212-1218.
29. During the preparation of this manuscript a related study was reported: Zhao, Q.; Han, F.; Romero, D. J. Org. Chem. 2002, 67, 3317-3322.
30. For synthetic procedures: (a) Tamura, O.; Gotanda, K.; Yoshino, J.; Morita, Y.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Mita, N.; Yamashita, M.; Ishibashi, H.; Sakamoto, M. J. Org. Chem. 2000, 65, 8544-8551.
31. (b) Polónski, T.; Chimiak, A. Tetrahedron Lett. 1974, 2453-2456.
32. Schleich, S.; Helmchen, G. Eur. J. Org. Chem. 1999, 2515-2521.
33. (a) Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324-2339.
34. (b) Kanemasa, S.; Tsuruoka, T.; Wada, E. Tetrahedron Lett. 1993, 34, 87-90.
35. (c) Kanemasa, S.; Tsuruoka, T. Chem. Lett. 1995, 49-50.
36. (a) The exact role of 2-propanol as an additive is not clear; however, we believe it increases the solubility and overall homogeneity of the intermediate chelated nitrone 2.
37. (b) For a review on additives in asymmetric synthesis: Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570-1577.
38. Synthesis of 9: Farquhar, D.; Cherif, A.; Bakina, E.; Nelson, J. A. J. Med. Chem. 1998, 41, 965-972. Synthesis of 7: Spino, C.; Barriault, N. J. Org. Chem. 1999, 64, 5292-5298.
39. Synthesis of 9: Farquhar, D.; Cherif, A.; Bakina, E.; Nelson, J. A. J. Med. Chem. 1998, 41, 965-972. Synthesis of 7: Spino, C.; Barriault, N. J. Org. Chem. 1999, 64, 5292-5298.
40. (a) Reference 6b.
41. (b) Broggini, G.; Folcio, F.; Sardone, N.; Sonzogni, M.; Zecchi, G. Tetrahedron: Asymmetry 1996, 7, 797-806.
42. (c) Reference 5j.
43. (a) Noteberg, D.; Branalt, J.; Kvarnstrom, I.; Classon, B.; Samuelsson, B.; Nillroth, U.; Danielson, U. H.; Karlen, A.; Hallberg, A. Tetrahedron 1997, 53, 7975-7984.
44. (b) Konosu, T.; Oida, S. Chem. Pharm. Bull. 1993, 41, 1012-1018.
45. (a) Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564-2566.
46. (b) Morris, P. E.; Kiely, D. E. J. Org. Chem. 1987, 52, 1149-1152.
47. Shiba, T.; Akiyama, H.; Umeda, I.; Okada, S.; Wakamiya, T. Bull. Chem. Soc. Jpn. 1982, 55, 899-903.
48. Foubelo, F.; Yus, M. Tetrahedron: Asymmetry 1996, 7, 2911-2922.
49. (a) Chang, Z.; Coates, R. M. J. Org. Chem. 1990, 55, 3464-3474.
50. (b) Chang, Z.; Coates, R. M. J. Org. Chem. 1990, 55, 3475-3483.