Synthetic applications of 1-aminoalkyl chloromethyl ketones. Synthesis of enantiopure 3-azetidinols and aminoalkyl epoxides

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5974-5977

  Barluenga, José ^a   Baragaña, Beatriz ^a   Concellón, José M ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 AZETIDINOL; ALKYL GROUP; AMINE; AZETIDINE; EPOXIDE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0030870532     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9700585     Document Type: Article

References (34)

1. Review: (a) Davies, D. E.; Storr, R. C. In Comprenhensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, pp 238-284. Other recent synthetic applications of azetidines; (b) Jung, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. (c) Viallon, L.; Reinand, O.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1995, 36, 4787.
2. Review: (a) Davies, D. E.; Storr, R. C. In Comprenhensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, pp 238-284. Other recent synthetic applications of azetidines; (b) Jung, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. (c) Viallon, L.; Reinand, O.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1995, 36, 4787.
3. Review: (a) Davies, D. E.; Storr, R. C. In Comprenhensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, pp 238-284. Other recent synthetic applications of azetidines; (b) Jung, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. (c) Viallon, L.; Reinand, O.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1995, 36, 4787.
4. (a) Testa, E.; Wittigens, A.; Meffii, G.; Bianchi, G. In Research Progress in Organic, Biological and Medical Chemistry; Gallo, U., Santamaria, L., Eds.; North-Holland Publishing Co.: Amsterdam, 1964; Vol. 1, pp 477-583.
5. (b) Okutani, T.; Kaneko, T.; Masuda, K. Chem. Pharm. Bull. 1974, 22, 1490.
6. (c) Kobayashi, J.; Cheng, J.; Ishibashi, M.; Wälchli, M. P.; Yamamura, S.; Ohizumi, Y. J. Chem. Soc., Perkin Trans. 1 1991, 1135.
7. (d) Frigola, J.; Torrens, A.; Castrillo, J. A.; Mas, J.; Vañö, D.; Berrocal, J. M.; Calvet, C.; Salgado, L.; Redondo, J.; García-Granda, S.; Valeñtí, E.; Quintana, J. R. J. Med. Chem. 1994, 37, 4195.
8. Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331.
9. Recently a synthesis of enantiomerically pure polysubstituted azetidines from 1,3-amino alcohols has been described: Barluenga, J.; Fernández-Marí, F.; Viado, A. L.; Aguilar, E.; Olano, B. J. Org. Chem. 1996, 61, 5659.
10. Ojima, I.; Zhao, M.; Yamato, T.; Nakahashi, K.; Yamashita, M.; Abe, R. J. Org. Chem. 1991, 56, 5263 and references cited therein.
11. (a) Poch, M.; Verdaguer, X.; Moyano, A.; Pericás, M. A.; Ríera, A. Tetrahedron Lett. 1991, 32, 6935.
12. (b) Hiraki, T.; Yamagiwa, Y.; Kamikawa, T. Tetrahedron Lett. 1995, 36, 4841.
13. (c) Takikawa, H.; Maeda, T.; Mori, K. Tetrahedron Lett. 1995, 36, 7689.
14. Wells, J. N. ; Tarwater, O. R. J. Pharm. Bull. 1974, 22, 1490.
15. 3-Azetidinols as racemic mixture have been prepared from l-(alkylamino)-3-chloro-2-alkanols: (a) Gaertner, V. R. J. Org. Chem. 1967, 32, 2972. (b) Higgins, R. H.; Eaton, Q. L.; Worth, L. Jr.; Peterson, M. V. J. Heterocycl. Chem. 1987, 24, 255.
16. 3-Azetidinols as racemic mixture have been prepared from l-(alkylamino)-3-chloro-2-alkanols: (a) Gaertner, V. R. J. Org. Chem. 1967, 32, 2972. (b) Higgins, R. H.; Eaton, Q. L.; Worth, L. Jr.; Peterson, M. V. J. Heterocycl. Chem. 1987, 24, 255.
17. Barluenga, J.; Baragana, B.; Alonso, A.; Concellón, J. M. J. Chem. Soc., Chem. Commun. 1994, 969.
18. Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1995, 60, 6696.
19. Moore, J. A.; Ayers, R. S. In The Chemistry of Heterocyclic Compounds. Small Ring Heterocycles; Hassner, A., Ed.; J. Wiley and Son.: New York, 1983; vol. 42, Part 2, p 11.
20. Amino epoxides are used in synthesis of several important compounds. See, for instance: amino sugars: (a) McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. (b) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50 and references cited therein. Polyoxygenated amino acids: (c) Hua, D. Y.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4. Hydroxyethylene dipeptide isosteres: (d) Thompson, W. J.; Fitzgerald, P. M. D.; Holloway, M. K.; Emini, E. A.; Darke, P. L.; Mckeever, B. M.; Schleif, W. A.; Quintero, J. C.; Zugay, J. A.; Tucker, T. J.; Schwering, J. E.; Homnick, C. F.; Numberg, J.; Springer, J. P.; Huff, J. R. J. Med. Chem. 1992, 35, 1685. (e) Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771. Peptidyl epoxides: (f) Albeck, A.; Fluss, S.; Persky, R. J. Am. Chem. Soc. 1996, 118, 3591.
21. Amino epoxides are used in synthesis of several important compounds. See, for instance: amino sugars: (a) McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. (b) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50 and references cited therein. Polyoxygenated amino acids: (c) Hua, D. Y.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4. Hydroxyethylene dipeptide isosteres: (d) Thompson, W. J.; Fitzgerald, P. M. D.; Holloway, M. K.; Emini, E. A.; Darke, P. L.; Mckeever, B. M.; Schleif, W. A.; Quintero, J. C.; Zugay, J. A.; Tucker, T. J.; Schwering, J. E.; Homnick, C. F.; Numberg, J.; Springer, J. P.; Huff, J. R. J. Med. Chem. 1992, 35, 1685. (e) Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771. Peptidyl epoxides: (f) Albeck, A.; Fluss, S.; Persky, R. J. Am. Chem. Soc. 1996, 118, 3591.
22. Amino epoxides are used in synthesis of several important compounds. See, for instance: amino sugars: (a) McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. (b) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50 and references cited therein. Polyoxygenated amino acids: (c) Hua, D. Y.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4. Hydroxyethylene dipeptide isosteres: (d) Thompson, W. J.; Fitzgerald, P. M. D.; Holloway, M. K.; Emini, E. A.; Darke, P. L.; Mckeever, B. M.; Schleif, W. A.; Quintero, J. C.; Zugay, J. A.; Tucker, T. J.; Schwering, J. E.; Homnick, C. F.; Numberg, J.; Springer, J. P.; Huff, J. R. J. Med. Chem. 1992, 35, 1685. (e) Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771. Peptidyl epoxides: (f) Albeck, A.; Fluss, S.; Persky, R. J. Am. Chem. Soc. 1996, 118, 3591.
23. Amino epoxides are used in synthesis of several important compounds. See, for instance: amino sugars: (a) McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. (b) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50 and references cited therein. Polyoxygenated amino acids: (c) Hua, D. Y.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4. Hydroxyethylene dipeptide isosteres: (d) Thompson, W. J.; Fitzgerald, P. M. D.; Holloway, M. K.; Emini, E. A.; Darke, P. L.; Mckeever, B. M.; Schleif, W. A.; Quintero, J. C.; Zugay, J. A.; Tucker, T. J.; Schwering, J. E.; Homnick, C. F.; Numberg, J.; Springer, J. P.; Huff, J. R. J. Med. Chem. 1992, 35, 1685. (e) Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771. Peptidyl epoxides: (f) Albeck, A.; Fluss, S.; Persky, R. J. Am. Chem. Soc. 1996, 118, 3591.
24. Amino epoxides are used in synthesis of several important compounds. See, for instance: amino sugars: (a) McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. (b) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50 and references cited therein. Polyoxygenated amino acids: (c) Hua, D. Y.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4. Hydroxyethylene dipeptide isosteres: (d) Thompson, W. J.; Fitzgerald, P. M. D.; Holloway, M. K.; Emini, E. A.; Darke, P. L.; Mckeever, B. M.; Schleif, W. A.; Quintero, J. C.; Zugay, J. A.; Tucker, T. J.; Schwering, J. E.; Homnick, C. F.; Numberg, J.; Springer, J. P.; Huff, J. R. J. Med. Chem. 1992, 35, 1685. (e) Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771. Peptidyl epoxides: (f) Albeck, A.; Fluss, S.; Persky, R. J. Am. Chem. Soc. 1996, 118, 3591.
25. Amino epoxides are used in synthesis of several important compounds. See, for instance: amino sugars: (a) McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. (b) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50 and references cited therein. Polyoxygenated amino acids: (c) Hua, D. Y.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4. Hydroxyethylene dipeptide isosteres: (d) Thompson, W. J.; Fitzgerald, P. M. D.; Holloway, M. K.; Emini, E. A.; Darke, P. L.; Mckeever, B. M.; Schleif, W. A.; Quintero, J. C.; Zugay, J. A.; Tucker, T. J.; Schwering, J. E.; Homnick, C. F.; Numberg, J.; Springer, J. P.; Huff, J. R. J. Med. Chem. 1992, 35, 1685. (e) Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771. Peptidyl epoxides: (f) Albeck, A.; Fluss, S.; Persky, R. J. Am. Chem. Soc. 1996, 118, 3591.
26. 13C NMR δ 5.7, 13.3, 22.4, 25.0, 35.0, 50.9, 54.8, 55.1, 75.7, 126.4, 127.6, 128.4, 139.2.
27. Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, T.; Mita, Y.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
28. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
29. (a) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141.
30. (b) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531.
31. Reetz, M. T.; Drewes, M. W.; Lennick, K.; Schmitz, A.; Holdgrün, X. Tetrahedron: Asymmetry 1990, 1, 375.
32. ElAmin, B.; Anantharamaiah, G. M.; Royer, G. P.; Means, G. E. J. Org. Chem. 1979, 44, 3442.
33. When intermediates 2 were hydrolyzed at room temperature, compounds 4 were isolated instead of epoxides 8.
34. Rittle, K. E.; Homnick, C. F.; Ponciello, G. S.; Evans, B. E. J. Org. Chem. 1982, 47, 3016.