Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides

Tetrahedron Asymmetry

Volumn 11, Issue 15, 2000, Pages 3079-3090

  Yuste, Francisco ^a   Ortiz, Benjamin ^a   Carrasco, Alejandra ^a   Peralta, Martha ^b   Quintero, Leticia ^b   Sánchez Obregón, Rubén ^a   Walls, Fernando ^a   García Ruano, José L ^c  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^c UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINOALCOHOL; SULFOXIDE;

ARTICLE; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034637349     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00264-0     Document Type: Article

References (72)

1. (a) Bergmeier, S. C. Tetrahedron 2000 56, 2561.
2. (b) Ager, J. D.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
3. (c) Tramontini, M. Synthesis 1982, 605.
4. (d) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
5. (e) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497.
6. Reiners, I.; Martens, J. H. Tetrahedron: Asymmetry 1997, 8, 277.
7. (a) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531.
8. (b) Reetz, M. T. Chem. Rev. 1999, 99, 1121.
9. (c) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.
10. (d) Laib, T.; Chastanet, J. J. Org. Chem. 1998, 63, 1709.
11. Kunieda, T.; Ishizuka, T. In Studies in Natural Product Chemistry; Atta-ur Rahman, Ed.; Elsevier: New York, 1993; Vol. 12, p. 411.
12. (a) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids; John Wiley & Sons: New York, 1987.
13. (b) Reetz, M. T.; Drewes, M. W.; Lennick, K.; Schmitz, A.; Holdgrün, X. Tetrahedron: Asymmetry 1990, 1, 375.
14. (c) Paleo, M. R.; Calaza, M. I.; Sardina F. J. J. Org. Chem. 1997, 62, 6862.
15. (d) Chung, S.-K.; Lee, J.-M. Tetrahedron: Asymmetry 1999, 10, 1441.
16. (e) Wagner, B.; Gonzalez, G. I.; Dau, M. E. T. H.; Zhu, J. Bioorg. Med. Chem. 1999, 7, 737.
17. (f) Methods of Organic Chemistry (Houben-Weyl), Vol. E21 (Stereoselective synthesis); Georg Thieme: Stuttgart, New York; p. 4013.
18. (a) Hou, X.-L.; Wu, J.; Dai, L.-X.; Xia, L.-J.; Tang, M.-H. Tetrahedron: Asymmetry 1998, 9, 1747.
19. (b) Anaya de Parrodi, C.; Juaristi, E.; Quintero, L. An. Química Int. Ed. 1996, 92, 400.
20. (c) Yamashita, H. Chem. Lett. 1987, 525.
21. Chang, H.-T.; Sharpless, K. B. Tetrahedron Lett. 1996, 37, 3219.
22. (a) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
23. (b) Nymann, K.; Mylvaganam, S.; Svendsen, J. S. Acta Chem. Scand. 1998, 52, 1060.
24. (a) García Ruano, J. L.; Alcudia, A.; Barros, D.; Fernandez, I.; Maestro, M. C.; Prado, M. J. Org. Chem. 2000, 65, 2856.
25. (b) Kiess, F.-M.; Pogendorf, P.; Picasso, S.; Jäger, V. J. Chem. Soc., Chem. Commun. 1998, 119.
26. (c) Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijama, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908.
27. (d) Coldham, I.; Holman, S.; Lang-Anderson, M. M. S. J. Chem. Soc., Perkin Trans. 1 1997, 1481.
28. (e) Barret, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677.
29. (a) Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.
30. (b) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1493.
31. (c) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810.
32. (d) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
33. (e) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385.
34. Enders, D.; Haertwig, A.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 1998, 1771, and references cited therein.
35. (a) Solladié, G.; Carreño, M. C. In Organosulphur Chemistry. Synthethic Aspects; Page, P. C. B., Ed.; Academic Press: New York, 1995; Chapter 1, pp. 1-47.
36. (b) Carreño M. C. Chem. Rev. 1995, 95, 1717, and references cited therein.
37. (a) Bueno, A. B.; Carreño, M. C.; Fischer, J.; García Ruano, J. L.; Peña, B.; Peñas, L.; Rubio, A. Tetrahedron Lett. 1991, 32, 3191.
38. (b) Bueno, A. B.; Carreño, M. C.; García Ruano, J. L. An. Quim. Int. Ed. 1994, 90, 442.
39. (c) Carreño, M. C.; García Ruano, J. L.; Maestro, M. C.; Pérez González, M.; Bueno, A. B.; Fisher, J. Tetrahedron 1993, 49, 11009.
40. (d) García Ruano, J. L.; García Paredes, C. Tetrahedron Lett. 2000, 41, 261.
41. (a) García Ruano, J. L.; Martín A. M.; Rodríguez, J. H. Tetrahedron Lett. 1991, 32, 5423.
42. (b) García Ruano, J. L.; Martín A. M.; Rodríguez, J. H. J. Org. Chem. 1992, 57, 7235.
43. (c) García Ruano, J. L.; Martín A. M.; Rodríguez, J. H. J. Org. Chem. 1994, 59, 533.
44. (d) Escribano, A.; García Ruano, J. L.; Martín A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567.
45. (e) García Ruano, J. L.; Martín A. M.; Rodríguez, J. H.; Rubio Flamarique, A. C. Tetrahedron: Asymmetry 1997, 8, 3503.
46. (a) Solladie, G.; Demailly, G.; Greck, C. Tetrahedron Lett. 1985, 26, 435.
47. (b) Carreño, M. C.; García Ruano, J. L.; Martín, A. M.; Pedregal, C.; Rodriguez, J. H.; Rubio, A.; Sánchez, J.; Solladié, G. J. Org. Chem. 1990, 55, 2120.
48. (c) Barros, D.; Carreño, M. C.; García Ruano, J. L.; Maestro, M. C. Tetrahedron Lett. 1992, 33, 2733.
49. For recent papers, see: (a) Solladié, G.; Hanquet, G.; Roland, C. Tetrahedron Lett. 1999, 40, 177. (b) Solladié, G.; Colobert, F.; Denni, D. Tetrahedron: Asymmetry 1998, 9, 3081.
50. For recent papers, see: (a) Solladié, G.; Hanquet, G.; Roland, C. Tetrahedron Lett. 1999, 40, 177. (b) Solladié, G.; Colobert, F.; Denni, D. Tetrahedron: Asymmetry 1998, 9, 3081.
51. (c) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martín Lomas, M.; García Ruano, J. L.; Solladié, G. J. Org. Chem. 1998, 63, 8918.
52. (d) Bueno, A. B.; Carreño, M. C.; García Ruano, J. L.; Gomez Arrayás, R.; Zarzuelo, M. M. J. Org. Chem. 1997, 62, 2139.
53. (e) García Ruano, J. L.; Gonzalez-Vadillo, A. M.; Maestro, C. Tetrahedron: Asymmetry 1997, 8, 3283.
54. (f) García-Ruano, J. L.; Maestro, M. C.; Barros, D. Tetrahedron: Asymmetry 1996, 7, 1819.
55. García Ruano, J. L.; Lorente, A.; Rodriguez, J. H. Tetrahedron: Asymmetry 1998, 9, 2437.
56. (a) García Ruano, J. L.; Lorente, A.; Rodriguez, J. H. Tetrahedron Lett. 1992, 33, 5637.
57. (b) García Ruano, J. L.; Cifuentes, M.; Lorente, A.; Rodriguez, J. H. Tetrahedron: Asymmetry 1999, 10, 4607.
58. Sánchez-Obregón, R.; Ortiz, B.; Walls, F.; Yuste, F.; García Ruano, J. L. Tetrahedron: Asymmetry 1999, 10, 947, and references cited therein.
59. García Ruano J. L.; García Paredes, C. Tetrahedron Lett. 2000, 41, 5357-5361.
60. Solladié, G. Synthesis 1981, 185.
61. (a) García Ruano, J. L.; Fuerte, A.; Maestro, M. C. Tetrahedron: Asymmetry 1994, 5, 1443.
62. (b) García-Ruano, J. L.; Maestro, M. C.; Sánchez-Sancho, F. Tetrahedron: Asymmetry 1995, 6, 2299.
63. (c) García-Ruano, J. L.; Barros, D.; González-Vadillo, A. M.; Maestro, M. C. Tetrahedron: Asymmetry 1996, 7, 1819.
64. (d) García-Ruano, J. L.; González-Vadillo, A. M; Maestro, M. C. Tetrahedron: Asymmetry 1997, 8, 3283.
65. Toscano, R. A.; Carrasco, A.; Ortiz, B.; Sánchez-Obregón, R.; Walls, F.; Yuste, F. Acta Crystallogr. 1999, C55, 1605.
66. Alcudia, F.; Brunet, E.; García Ruano, J. L.; Hoyos, M. A.; Prados, P.; Rodriguez, J. H. Org. Magn. Reson. 1983, 21, 643.
67. 2 reductions suggests that the evolution of other substituted α-alkylsulfoxides will also be highly stereoselective, thus allowing the synthesis of other alkyl carbinols with the limitations indicated in Ref. 15c.
68. García Ruano, J. L.; García Paredes, C.; Handouchi, C. Tetrahedron: Asymmetry 1999, 10, 2935, and references cited therein.
69. Prelog, V.; Mutak, S. Helv. Chim. Acta 1983, 66, 2274.
70. Schwerdtfeger, J.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1505.
71. Dickey, F. H.; Fickett, W.; Lucas, H. J. J. Am. Chem. Soc. 1952, 74, 944.
72. Seebach, D.; Charczuk, R.; Gerber, C.; Renaud, P.; Berner, H.; Schneider, H. Helv. Chim. Acta 1989, 72, 401.