A general synthesis of enantiopure 1,2-aminoalcohols via chiral morpholinones

Tetrahedron

Volumn 56, Issue 2, 2000, Pages 233-248

  Segat Dioury, Fabienne ^a   Lingibé, Olivier ^a   Graffe, Bernadette ^a   Sacquet, Marie Claude ^a   Lhommet, Gérard ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Aminoalcohols; Asymmetric induction; Imines; Reduction

Indexed keywords

AMINOALCOHOL; MORPHOLINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034614567     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00935-7     Document Type: Article

References (61)

1. Coppola G.M., Schuster H.F. Asymmetric Synthesis - Construction of Chiral Molecules using Amino-Acids. 1987;Wiley, New York.
2. (a) Célimène, C.; Dhimane, H.; Le Bail, M.; Lhommet, G. Tetrahedron Lett. 1994, 35, 6105.
3. (b) Grandjean, C. Thèse Université Paris VI, 13 Juillet 1994.
4. (a) Bonin, M.; Grierson, D. S.; Royer, J.; Husson, H. P. Org. Synth. 1992, 70, 54.
5. (b) Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 83.
6. (c) Evans, D. A.; Cameron Black, W. J. Am. Chem. Soc. 1993, 115, 4497.
7. (a) Kobayashi, S.; Murakami, M.; Harada, T.; Mukaiyama, T. Chem. Lett. 1991, 1341.
8. (b) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1995, 36, 613.
9. Gallagher D.J., Wu S., Nikolic N.A., Beak P. J. Org. Chem. 60:1995;8148.
10. (a) Grandbois, E. R.; Howard, S. I.; Morrison, J. D. In Asymmetric Synthesis; Vol. 2: Stereodifferentiating Addition Reactions, Part A; Academic Press: New York, 1985; Chapter 3, p 81.
11. (b) Falorni, M.; Collu, C.; Giacomelli, G. Tetrahedron: Asymmetry 1996, 7, 2739.
12. (c) Reiners, I.; Martens, J.; Schwarz, S.; Henkel, H. Tetrahedron: Asymmetry 1996, 7, 1763.
13. (a) Abiko, A.; Masamume, S. Tetrahedron Lett. 1992, 33, 5517.
14. (b) Meyers, A. I.; Elworthy, T. R. J. Org. Chem. 1992, 57, 4732.
15. (c) Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77.
16. (d) Genevois-Borella, A.; Monneret, C.; Florent, J. C.; Grierson, D. S. Tetrahedron Lett. 1990, 31, 4879.
17. (e) Andres, J. M.; Barrio, R.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. J. Org. Chem. 1996, 61, 4210.
18. (f) Mordini, A.; Valacchi, M.; Pecchi, S.; Degl'Innocenti, A.; Reginato, G. Tetrahedron Lett. 1996, 37, 5209.
19. (a) Fernandez, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2885.
20. (b) Ishizuka, T.; Kimura, K.; Ishibuchi, S.; Kunieda, T. Chem. Lett. 1992, 991.
21. (a) Iuliano, A.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1995, 6, 739.
22. (b) Ishimaru, K.; Tsuru, K.; Yabuta, K.; Wada, M.; Yamamoto, Y.; Akiba, K.-Y. Tetrahedron 1996, 52, 13137.
23. (a) Umezawa, J.; Takahashi, O.; Furuhashi, K.; Nohira, H. Tetrahedron: Asymmetry 1994, 5, 491.
24. (b) Senanayake, C. H.; Larsen, R. D.; DiMichele, L. M.; Liu, J.; Toma, P. H.; Ball, R. G.; Verhoeven, T. R.; Reider, P. J. Tetrahedron: Asymmetry 1996, 7, 1501.
25. Hwang G.I., Chung J.H., Lee W.K. J. Org. Chem. 61:1996;6183.
26. (a) Dellaria, J. F.; Santarsiero, B. D. Tetrahedron Lett. 1988, 27, 6079.
27. (b) Harwood, L. M.; Tyler, S. N. G.; Anslow, A. S.; MacGilp, I. D.; Drew, M. G. B. Tetrahedron: Asymmetry 1997, 8, 4007.
28. Greenstein J.P., Winitz M. Chemistry of the Amino Acids. Vol. 2:1961;890-895 Wiley, New York.
29. Bacos D., Basselier J.J., Célérier J.P., Lange C., Marx E., Lhommet G., Escoubas P., Lemaitre M., Clément J.L. Tetrahedron Lett. 29:1988;3061.
30. Caplar V., Lisini A., Kajfez F., Kolbah D., Sunjic V. J. Org. Chem. 43:1978;1355.
31. Unreacted aminoacid 8 and side product 11 were always isolated from the crude materials. The side product 11 may arise from the following acido-basic equilibrium followed by anionic condensation
32. The Z-isomer of 7a is only formed as it is highly stabilised by an intramolecular hydrogen bond between the hydrogen on the nitrogen atom and the ester carbonyl group, see Célérier, J. P.; Deloisy-Marchalant, E.; Lhommet, G. J. Heterocycl. Chem. 1633, 21, 1984.
33. (a) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051.
34. (b) Ager, D.; Cooper, N.; Cox, G. G.; Garro-Hélion, F.; Harwood, L. M. Tetrahedron: Asymmetry 1996, 7, 2563.
35. 1H NMR.
36. If the alkylating agent was not added, the dihydro oxazole 15 was isolated in 36% yield after chromatography. In prolonged reflux of toluene (without sodium hydride) or at room temperature with sodium hydride, the dihydro oxazole 15 was not formed, the enaminoester 7a was entirely recovered.
37. Johnson A.W., Marklam E., Price R. Org. Synth. 42:1962;75.
38. (a) De Kimpe, N.; de Cock, W. Synthesis 1987, 188.
39. (b) Salih, M. A.; Compernolle, F.; Van den Branden, S.; De Buysser, W.; Hoornaert, G. J. Org. Chem. 1993, 58, 690.
40. Marquet A., Gaudry M. Org. Synth. 55:1976;24.
41. Lingibé O., Graffe B., Sacquet M.-C., Lhommet G. Heterocycles. 37:1994;1469.
42. Segat F., Lingibé O., Graffe B., Sacquet M.-C., Lhommet G. Heterocycles. 45:1997;1451.
43. Giannis A., Sandhoff K. Angew. Chem., Int. Ed. Engl. 28:1989;218.
44. These bicyclic lactams 23b, c were obtained in quantitative yields by refluxing compounds 17b, c in toluene (20 and 10 h, respectively); yield: 85% for 23b and 92% for 23c.
45. (a) Schöllkopf, U.; Scheuer, R. Liebigs Ann. Chem. 1984, 939.
46. (b) Schöllkopf, U.; Scheuer, R. Liebigs Ann. Chem. 1982, 1952.
47. Meerwein H. Org. Synth. 46:1966;113.
48. Undheim K., Benneche T., Christiansen M.L. Acta Chem. Scand. Ser. B. 40:1986;700.
49. Capozzi G., Romeo G., Lucchini V., Modena G. J. Chem. Soc., Perkin Trans 1. 1983;831.
50. Guetté J.P., Spassky N. Bull. Soc. Chim. Fr. 1972;4217.
51. Francalanci F., Cesti P., Cabri W., Bianchi D., Martinengo T., Foà M. J. Org. Chem. 52:1987;5079.
52. Meyers A.I., Dickman D.A., Bailey T.R. J. Am. Chem. Soc. 107:1985;7974.
53. Pointdexter G.S., Meyers A.I. Tetrahedron Lett. 17:1997;3527.
54. Romo D., Romine J.L., Midura W., Meyers A.I. Tetrahedron. 46:1990;4951.
55. Fujisawa T., Mori T., Sato T. Chem. Lett. 1983;835.
56. Ripperger H., Schreiber K. Tetrahedron. 21:1965;1485.
57. 20 of 20a and 20b are identical to those of aminoalcohols obtained from reduction of L-aspartic and L-glutamic acids, respectively.
58. (a) Handrick, G. R.; Atkinson, E. R. J. Med. Chem. 1966, 9, 558.
59. (b) Sandrin, E.; Bauer, W. U.S. Patent 4,291,022-22, 1981.
60. Karrer P., Portmann P. Helv. Chem. Acta. 31:1948;2088.
61. Friedman O.M., Boyer E. J. Am. Chem. Soc. 78:1956;4659.