N-thioacyl 1,3-amino alcohols: Synthesis via ring-opening of oxiranes with thioamide dianions and applications as key intermediates leading to stereochemically defined 5,6-dihydro-4H-1,3-oxazines and 1,3-amino alcohols

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 8148-8153

  Murai, Toshiaki ^a   Sano, Hiroaki ^a   Kawai, Hiroyasu ^a   Aso, Hideo ^a   Shibahara, Fumitoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; COLUMN CHROMATOGRAPHY; LITHIUM COMPOUNDS; MOLECULAR DYNAMICS; NEGATIVE IONS; PARAFFINS; REACTION KINETICS; STEREOCHEMISTRY;

N-THIOACYL 1,3-AMINO ALCOHOLS; REGIOSELECTIVITY; RING-OPENING; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

ALCOHOL DERIVATIVE; ALKYL GROUP; AMINE; AMINOALCOHOL; ANION; ETHYLENE OXIDE DERIVATIVE; LITHIUM DERIVATIVE; OXAZINE DERIVATIVE; THIOAMIDE;

ARTICLE; COLUMN CHROMATOGRAPHY; CYCLIZATION; DIASTEREOISOMER; OPTICAL ROTATION; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; SEPARATION TECHNIQUE; STEREOCHEMISTRY; SYNTHESIS;

AMINO ALCOHOLS; ANIONS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXAZINES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; THIOAMIDES;

EID: 25444443969     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051378o     Document Type: Article

References (63)

1. (a) Lawson, A.; Searle, C. E. J. Chem. Soc. 1957, 1556.
2. (b) Laduron, F.; Nyns, C.; Janousek, Z.; Viehe, H. G. J. Prakt. Chem. 1997, 339, 697.
3. (c) Wipf, P.; Hayes, G. B. Tetrahedron 1998, 54, 6987.
4. (d) Leflemme, N.; Dallemagne, P.; Rault, S. Tetrahedron Lett. 2004, 45, 1503.
5. (a) Brossmer, R.; Isecke, R.; Herrler, G. FEBS Lett. 1993, 323, 96.
6. (b) Brossmer, R.; Gross, H. J. Methods Enzymol. 1994, 247, 153.
7. (c) Terada, T.; Kitajima, K.; Inoue, S.; Koppert, K.; Brossmer, R.; Inoue, Y. Eur. J. Biochem. 1996, 236, 852.
8. (d) Brossmer, R.; Klenk, H.-D.; Herrler, G. Virology 1996, 218, 127.
9. (e) Guzaev, A. P.; Manoharan, M. J. Am. Chem. Soc. 2001, 123, 783.
10. (f) Hwang, O.; Kim, G.; Jang, Y. J.; Kim, S. W.; Choi, G.; Choi, H. J.; Jeon, S. Y.; Lee, D. G.; Lee, J. D. Mol. Pharm. 2001, 59, 1249.
11. (a) Sicher, J.; Pankova, M.; Jonas, J. Svoboda, M. Collect. Czech. Chem. Commun. 1959, 24, 2727.
12. (b) Drefahl, G.; Horhold, H. H. Chem. Ber. 1961, 94, 1641.
13. (c) Legrand, L.; Lozac'h, N. Phosphorus Sulfur Relat. Elem. 1986, 26, 111.
14. (c) Isecke, R.; Brossmer, R. Tetrahedron 1994, 50, 7445.
15. (d) Katritzky, A. R.; Moutou, J.-L. Yang, Z. Synthesis 1995, 1497.
16. Haske, B. J.; Matthews, M. E.; Conkling, J. A.; Perzanowski, H. P. J. Org. Chem. 1967, 32, 1579.
17. For reviews, see: (a) Metzner, P. In Topics in Current Chemistry; Page, P. C. B., Ed.; Springer-Verlag: Berlin, 1999; Vol. 204, p 127.
18. (b) Murai, T. In Topics in Current Chemistry; Kato, S., Ed.; Springer-Verlag: Berlin, 2005; Vol. 251, p 247.
19. (a) Murai, T.; Aso, H.; Tatematsu, Y.; Itoh, Y.; Niwa, H. J. Org. Chem. 2003, 68, 8514.
20. (b) Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968.
21. (c) Murai, T.; Ohta, Y.; Mutoh, Y. Tetrahedron Lett. 2005, 46, 3637.
22. For recent reviews of the synthesis of oxiranes, see: (a) Lane, B. S.; Burgess, K.; Chem. Rev. 2003, 103, 2457.
23. (b) Shi, Y. Acc. Chem. Res. 2004, 37, 488.
24. (c) Yang, D. Acc. Chem. Res. 2004, 37, 497.
25. (d) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
26. The two diastereomers of N-thioacyl 1,3-amino alcohols 4 were easily distinguished on the basis of their light yellow color during the column purification.
27. 10 In contrast, regioselective ring-opening of 3f with thioamide dianion 2a was achieved even in the absence of Lewis acids.
28. (a) Imogai, H.; Larcheveque, M. Tetrahedron: Asymmetry 1997, 8, 965.
29. (b) Botuha, C.; Haddad, M.; Larcheveque, M. Tetrahedron: Asymmetry 1998, 9, 1929.
30. For details, see the Supporting Information.
31. For recent examples, see: (a) Liu, S.; Müller, J. F. K.; Neuburger, M.; Schaffner, S.; Zehnder, M. Helv. Chim. Acta 2000, 83, 1256.
32. (b) Kuznetsov, V. V.; Brusilovskii, Y. E. Chem. Heterocycl. Commun. 2001, 37, 574.
33. (c) Nakajima, N.; Saito, M.; Kudo, M.; Ubukata, M. Tetrahedron 2002, 58, 3579.
34. (d) Gaulon, C.; Gizecki, P.; Dhal, R.; Dujardin, G. Synlett 2002, 952.
35. (e) Nakajima, N.; Isobe, T.; Irisa, S.; Ubukata, M. Heterocycles 2003, 59, 107.
36. (f) Palko, M.; Hetenyi, A.; Fueloep, F. J. Heterocycl. Chem. 2004, 41, 69.
37. (g) Tse, M. K.; Doebler, C.; Bhor, S.; Klawonn, M.; Maegerlein, H. H. Beller, M. Angew. Chem., Int. Ed. 2004, 43, 5255.
38. (a) Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585.
39. (b) Katritzky, A. R.; Ghiviriga, I.; Chen, K.; Tymoshenko, D. O.; Abdel-Fattah, A. A. A. J. Chem. Soc., Perkin Trans. 2 2001, 530.
40. (c) Gizecki, P.; Dhal, R.; Poulard, C.; Gosselin, P.; Dujardin, G. J. Org. Chem. 2003, 68, 4338.
41. Nishio, T.; Konno, Y.; Ori, M.; Sakamoto, M. Eur. J. Org. Chem. 2001, 3553.
42. For recent examples of the stereoselective syntheses of 1-aryl-1,3-amino alcohols, see: (a) Cicchi, S.; Bonanni, M.; Cardona, F.; Revuelta, J.; Goti, A. Org. Lett. 2003, 5, 1773.
43. (b) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
44. (c) Kuethe, J. T.; Comins, D. L. Tetrahedron Lett. 2003, 44, 4179.
45. (d) Rezaei, M.; Harris, T. M.; Rizzo, C. J. Tetrahedron Lett. 2003, 44, 7513.
46. (e) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018.
47. (f) Minter, A.; Fuller, A. A.; Mapp, A. K. J. Am. Chem. Soc. 2003, 125, 6846.
48. (g) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
49. (h) Kochi, T.; Tang, T. P. Ellman, J. A. J. Am. Chem. Soc. 2003, 125, 11276.
50. (i) Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178.
51. (j) Bernardi, L.; Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Folegatti, M.; Grilli, S.; Mazzanti, A.; Ricci, A. Tetrahedron: Asymmetry 2004, 15, 245.
52. (k) Rodriquez, A. C.; Ramos, A. P.; Hawkes, G. E.; Berti, F.; Resmini, M. Tetrahedron: Asymmetry 2004, 15, 1847.
53. (l) Revuelta, J.; Cicchi, S.; Brandi, A. Tetrahedron 2004, 45, 8375.
54. (m) Matsubara, R.; Vital, P.; Nakamura, Y.; Kiyohara, H.; Kobayashi, S. Tetrahedron 2004, 60, 9769.
55. (n) Kennedy, A.; Nelson, A.; Perry, A. Synlett, 2004, 967.
56. (o) Chandrasekhar, S.; Babu, B. N.; Ahmed, M.; Reddy, M. V.; Jagadeesh, S. B. Synlett 2004, 1303.
57. (p) Fuller, A. A.; Chen, B.; Minter, A. R.; Mapp, A. K. Synlett 2004, 1409.
58. (q) Cordova, A. Chem. Eur. J. 2004, 10, 1987.
59. (a) Seebach, D.; Lubosch, W.; Enders, D. Chem. Ber. 1976, 109, 1309.
60. (b) Lubosch, W.; Seebach, D. Helv. Chim. Acta 1980, 63, 102.
61. (c) Goasdoue, C.; Gaudemar, M.; Mladenova, M. J. Organomet. Chem. 1981, 208, 279.
62. (d) Goasdoue, C.; Goasdoue, N.; Gaudemar, M. J. Organomet. Chem. 1984, 263, 273.
63. 2O gave the desired product 9c.