Asymmetric synthesis of (2R,3S)-4-halo-3-benzyloxy-2-(N-methoxycarbonyl-N-benzylamino)butyronitriles as precursors for the synthesis of β-hydroxy-α-amino acids

Tetrahedron Asymmetry

Volumn 11, Issue 4, 2000, Pages 1015-1025

  Badorrey, Ramón ^a   Cativiela, Carlos ^a   Díaz De Villegas, María D ^a   Gálvez, José A ^a  

^a INSTITUTO DE CIENCIA DE MATERIALES DE ARAGÓN   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZYLAMINO 3 BENZYLOXY 4 (TERT BUTYLDIMETHYLSILYLOXY)BUTYRONITRILE; 2 BENZYLOXY 1 (N METHOXYCARBONYL N BENZYLAMINO)CYCLOPROPANECARBOXAMIDE; GLYCERALDEHYDE; HYDROXYAMINO ACID; N BENZYLIMINE; NITRILE; REAGENT; SERINE DERIVATIVE; TRIMETHYLSILYL CYANIDE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CONTROLLED STUDY; CYCLIZATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0034629074     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00022-7     Document Type: Article

References (86)

1. (a) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
2. (b) Saeed, A.; Young, D. W. Tetrahedron 1992, 48, 2507-2514.
3. (a) Amino Acids, Peptides and Proteins; Specialist Periodical Reports; Chem. Soc.: London, 1968-1995; Vols 1-28.
4. (b) See Ref. 2 in Blaskovich, M. A.; Evindar, G.; Rose, N. G. W.; Wilkinson, S.; Luo, Y.; Lajoie, G. A. J. Org. Chem. 1998, 63, 3631-3646.
5. (a) Floyd, D. M.; Fritz, A. W.; Plusec, J.; Weaver, E. R.; Cimarusti, C. M. J. Org. Chem. 1982, 47, 5160-5167.
6. (b) Labia, R.; Morin, C. J. Antibiot. 1984, 37, 1103-1129.
7. (c) Miller, M. J. Acc. Chem. Res. 1986, 19, 49-56.
8. (d) Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618-625.
9. Golebiowski, A.; Jurczak, J. Synlett 1993, 241-245.
10. Cossu, S.; Conti, S.; Giacomelli, G.; Farloni, M. Synthesis 1994, 1429-1432.
11. Pansare, S. V.; Veredas, J. C. J. Org. Chem. 1987, 52, 4804-4810.
12. (a) Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866-1875.
13. (b) Williams, L.; Zhang, Z.; Ding, X.; Joullié, M. M. Tetrahedron Lett. 1995, 36, 7031-7034.
14. (c) Kumar, J. S. R.; Datta, A. Tetrahedron Lett. 1997, 38, 473-476.
15. (d) Laïb, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771-1772.
16. (e) Blaskovich, M. A.; Evindar, G.; Rose, N. G. W.; Wilkinson, S.; Luo, Y.; Lajoie, G. A. J. Org. Chem. 1998, 63, 3631-3646.
17. (f) Veeressa, G.; Datta, A. Tetrahedron Lett. 1998, 39, 3069-3070.
18. (a) Guanti, J.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553-5562.
19. (b) Girard, A.; Greck, C.; Ferroud, D.; Genêt, J. P. Tetrahedron Lett. 1996, 37, 7967-7970.
20. (c) Sting, A. R.; Seebach, D. Tetrahedron 1996, 52, 279-290.
21. (a) Cardani, S.; Bernardi, A.; Colombo, L.; Gennari, C.; Scolastico, C.; Venturini, I. Tetrahedron 1988, 44, 5563-5572.
22. (b) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
23. (c) Schmidt, U.; Respondek, M.; Lieberknecht, A.; Werner, J.; Fischer, P. Synthesis 1989, 256-261.
24. (d) Genet, J. P. Pure Appl. Chem. 1996, 68, 593-596.
25. (e) Pégorier, L.; Haddad, M.; Larchevêque, M. Synlett 1996, 585-586.
26. (f) Righi, G.; Chionne, A.; D'Achille, R.; Bonini, C. Tetrahedron: Asymmetry 1997, 8, 903-907.
27. (g) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. J. Org. Chem. 1998, 63, 3458-3462.
28. (a) Rao, A. V. R.; Chakraborty, T. K.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 5043-5046.
29. (b) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802.
30. (c) Shao, H.; Goodman, M. J. Org. Chem. 1996, 61, 2582-2583.
31. (d) Li, G.; Chang, H. T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454.
32. (e) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813-2817.
33. (f) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507-2510.
34. (a) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401-1406.
35. (b) Easton, C. J.; Hutton, C. A.; Roselt, P. D.; Tiekink, E. R. T. Tetrahedron 1994, 50, 7327-7340.
36. (c) Fernández-Megía, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643-7652.
37. (d) Albarez-Ibarra, C.; Csákÿ, A. G.; Ramirez, D. Tetrahedron 1997, 53, 2189-2198.
38. (e) Coulon, E.; Caño de Andrade, M. D.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Tetrahedron Lett. 1998, 39, 6467-6470.
39. (a) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151-7157.
40. (b) Ito, Y.; Sawamura, M.; Kobayashi, M.; Hayashi, T. Tetrahedron Lett. 1988, 29, 6321-6324.
41. (c) Casella, L.; Gullotti, M.; Jommi, G.; Pagliarin, R.; Sisti, M. J. Chem. Soc., Perkin Trans. 2 1990, 771-775.
42. (d) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827-830.
43. (e) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067-1078.
44. (f) Beulshausen, T.; Groth, U.; Schöllkopf, U. Liebigs Ann. Chem. 1991, 1207-1209.
45. (g) van der Werf, A. W.; Kellogg, R. M.; van Bolhuis, F. J. Chem. Soc., Chem. Commun. 1991, 682-683.
46. (h) Belokon, Y. N. Pure Appl. Chem. 1992, 64, 1917-1924.
47. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Y. T.; Raevsky, N. I.; Belokon, Y. N. Tetrahedron: Asymmetry 1995, 6, 1741-1756.
48. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550.
49. (k) Ferey, V.; Le Gall, T.; Mioskowski, C. J. Chem. Soc., Chem. Commun. 1995, 487-489.
50. (l) Solladié-Cavallo, A.; Nsenda, T. Tetrahedron Lett. 1998, 39, 2191-2194.
51. (m) Harwood, L. M.; Robertson, S. M. Chem. Commun. 1998, 2641-2642.
52. (m) Saeed, A.; Young, D. W. Tetrahedron 1992, 48, 2507-2514.
53. (n) Vassilev, V. P.; Uchiyama. T.; Kajimoto, T.; Wong, C. H. Tetrahedron Lett. 1995, 36, 4081-4084.
54. (o) Kimura, T.; Vassilev, V. P.; Shen, G. J.; Wong, C. H. J. Am. Chem. Soc. 1997, 119, 11734-11742.
55. (p) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846.
56. (a) Hirama, M.; Hioki, H.; Itô, S. Tetrahedron Lett. 1988, 29, 3125-3128.
57. (b) Krol, W. J.; Mao, S. S.; Steele, D. L.; Townsend, C. A. J. Org. Chem. 1991, 56, 728-731.
58. (c) Genet, J. P.; Pinel, C.; Mallart, S.; Juge, S.; Thorimbert, S.; Laffitte, J. A. Tetrahedron: Asymmetry 1991, 2, 555-567.
59. (d) Zandbergen, P.; Brussee, J.; van der Gen, A.; Kruse, C. G. Tetrahedron: Asymmetry 1992, 3, 769-774.
60. (e) Blank, S.; Seebach, D. Liebigs Ann. Chem. 1991, 889-896.
61. (f) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440.
62. (g) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754.
63. (h) Bycroft, M.; Herbert, R. B.; Ellames, G. J. J. Chem. Soc., Perkin Trans. 1 1996, 2439-2440.
64. (i) delle Monache, G.; Di Giovanni, M. C.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1997, 8, 231-243.
65. (j) Ciufolini, M. A.; Shimizu, T.; Swaminathan, S.; Xi, N. Tetrahedron Lett. 1997, 38, 4947-4950.
66. (k) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Tetrahedron Lett. 1997, 38, 6953-6956.
67. (l) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 3489-3496.
68. (m) Fadnavis, N. W.; Sharfuddin, M.; Vadivel, S. K.; Bhalerao, U. T. J. Chem. Soc., Perkin Trans. 1 1997, 3577-3578.
69. (n) Kuwano, R.; Okuda, S.; Ito, Y. J. Org. Chem. 1998, 63, 3499-3503.
70. (o) Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089-6098.
71. (p) Adams, Z. M.; Jackson, R. F. W.; Palmer, N. J.; Rami, H. K.; Wythes, M. J. J. Chem. Soc., Perkin Trans. 1 1999, 937-947.
72. (q) Boukhris, S.; Souizi, A. Tetrahedron Lett. 1999, 40, 1669-1672.
73. (a) Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron Lett. 1995, 36, 2859-2860.
74. (b) Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A.; García, J. A. Tetrahedron 1996, 52, 9563-9574.
75. Reetz, M. T.; Kusseler, K. J. Org. Chem. 1985, 50, 5434-5436.
76. Salaün, J.; Blaird, M. S. Curr. Med. Chem. 1995, 2, 511-542.
77. (a) Toniolo, C.; Crisma, M.; Valle, G.; Bonora, G. M.; Barone, B.; Benedetti, E.; Blasio, B. D.; Pavone, V.; Pedone, C.; Santini, A.; Lelj, F. Pept. Chem. 1987, 45.
78. (b) Burgess, K.; Ho, K.-K.; Pettitt, B. M. J. Am. Chem. Soc. 1995, 117, 54-65.
79. (c) Burgess, K.; Ho, K.-K.; Pal, B. J. Am. Chem. Soc. 1995, 177, 3808-3819.
80. (a) Stammer, C. H. Tetrahedron 1990, 46, 2231-2254.
81. (b) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett 1994, 575-583.
82. (c) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 87, 12721-12732.
83. Gaucher, A.; Ollivier, J.; Marguerite, J.; Paugam, R.; Salaün, J. Can. J. Chem. 1994, 72, 1312-1327.
84. March, J. Advanced Organic Chemistry: Reactions, Mechanisms & Structures; 4th ed.; John Wiley & Sons: New York, 1985; p. 156.
85. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Cryst. 1994, 27, 435-436.
86. Sheldrick, G. M. SHELXL-93. Program for the Refinement of Crystal Structures. University of Göttingen, Germany, 1993.