A new methodology for the synthesis of β-amino acids

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 9, 2000, Pages 1461-1466

  Sibi, Mukund P ^a   Deshpande, Prasad K ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ESTERS; ISOMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

PRECURSORS;

AMINO ACIDS;

EID: 0034616482     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908747h     Document Type: Article

References (78)

1. For a discussion of the synthesis and biology of β-amino acids sec: Enantioselective Synthesis of β-Amino Acids, ed. E. Juaristi, Wiley-VCH, New York, 1997; For comprehensive reviews on β-amino acids see:
2. D. C. Cole, Tetrahedron 1994, 50, 9517;
3. E. Juaristi, D. Quintana and J. Escalante, Aldrichimica Acta, 1994, 27, 3.
4. For a recent review on β-peptides see: S. H. Gellman, Acc. Chem. Res., 1998, 31, 173;
5. (a) S. Shinagawa, T. Kanamaru, S. Harada, M. Asai and H. Okazaki, J. Med. Chem., 1987, 30, 1458;
6. (b) A. Bongini, G. Cardillo, M. Orena, G. Porzi and S. Sandri, Tetrahedron, 1987, 43, 4377;
7. (c) N. Kabawata, T. Inamoto and S. Hashimoto, J. Antibiot., 1992, 45, 513;
8. (d) H. Oki, M. Hirano, K. Tomatsu, K. I. Numata and H. Kamei, J. Antibiot., 1989, 42, 1756;
9. (e) G. Casiraghi, L. Colombo, G. Rassu and P. Spanu, J. Org. Chem., 1991, 56, 6523;
10. (f) F. Matsuura, Y. Hamada and T. Shioiri, Tetrahedron, 1994, 50, 11303;
11. (g) M. F. Beatty, C. J. White and M. A. Avery, J. Chem. Soc., Perkin Trans, 1, 1992, 1637.
12. (a) F. Gueritte-Voegelein, V. Senilh, B. David, D. Guenard and P. Potier, Tetrahedron, 1986, 42, 4451;
13. (b) L. Mangatal, M. T. Adeline, D. Guenard and F. Gueritte-Voegelein, Tetrahedron, 1989, 45, 4177.
14. K. Iizuka, T. Kamijo, H. Harada, K. Akahane, T. Kubota, H. Umeyama and Y. Kiso, J. Chem. Soc., Chem. Commun., 1989, 1678.
15. For conversion of β-amino acids to β-lactams see: (a) N. Mayachi and M. Shibasaki, J. Org. Chem., 1990, 55, 1975;
16. (b) D. Tanner and P. Somfai, Tetrahedron, 1988, 44, 613.
17. (a) D. Guérnard, F. Gueritte-Voegelein and P. Potier, Acc. Chem. Res., 1993, 26, 160 and references cited therein;
18. (b) P. Potier, Chem. Soc. Rev., 1992, 21, 113.
19. For general information see: P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon: Oxford, 1992.
20. For a selected example see D. Enders, H. Wahl and W. Bettray, Angew. Chem., Int. Ed. Engl., 1995, 34, 455.
21. (a) I. Brackenridge, S. G. Davies, D. T. Fenwick, O. Ichihara and M. E. C. Polywka, Tetrahedron, 1999, 55, 533 and references therein;
22. (b) M. E. Bunnage, A. N. Chernega, S. G. Davies and C. J. Goodwin, J. Chem. Soc., Perkin Trans. J. 1994, 2373. For related work see:
23. J. M. Hawkins and T. A. Lewis, J. Org. Chem., 1994, 59, 649;
24. E. Juaristi, J. Escalante, B. Lamatsch and D. Seebach, J. Org. Chem., 1992, 57, 2396.
25. F. Dumas, B. Mezrhab and J. d'Angelo, J. Org. Chem., 1996, 61, 2293.
26. (a) F. A. Davis, P. Zhou and B.-C. Chen, Chem. Soc. Rev., 1998, 27, 13 and references therein; also see:
27. (b) T. R Tang and J. A. Ellman, J.Org. Chem., 1998, 64, 12.
28. (a) D. Seebach, A. Boog and W. B. Schweizer, Eur. J. Org. Chem., 1999, 335 and references therein;
29. (b) T. Hintermann and D. Seebach, Synlett, 1997, 437; also see
30. D. Seebach and H. Estermann, Tetrahedron Lett., 1987, 28, 3103.
31. (a) E. Juaristi, D. Quintana, B. Lamatsch and D. Seebach, J. Org. Chem., 1991, 56, 2553;
32. (b) E. Juaristi and D. Quintana, Tetrahedron: Asymmetry, 1992, 3, 723;
33. E. Juaristi, M. Balderas and X. Ramirez-Quirós, Tetrahedron: Asymmetry, 1998, 9, 3881.
34. (a) K. S. CHu, G. R. Negrete, J. P. Konopelski, F. J. Lakner, N.-T. Woo and M. M. Olmstead, J. Am. Chem. Soc., 1992, 114, 1800;
35. (b) K. S. Chu, G. R. Negrete and J. P. Konopelski, Tetrahedron, 1993, 49, 9183.
36. For an alternate synthesis of β-amino acids using oxazolidinones see: E. Arvanitis, H. Ernst, A. A. Ludwig, A. J. Robinson and P. B. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1998, 521; also
37. see: T. Hintermann and D. Seebach, Helv. Chim. Acta, 1998, 81, 2093.
38. D. A. Evans, L. D. Wu, J. J. M. Wiener, J. S. Johnson, D. H. B. Ripin and J. S. Tedrow, J. Org. Chem., 1999, 64, 6411.
39. L. Falborg and K. A. Jorgensen, J. Chem. Soc., Perkin Trans, 1, 1996, 2823.
40. (a) T. Ishikawa, K. Nagai, M. Senzaki, A. Tatsukawa and S. Saito, Tetrahedron, 1998, 54, 2433;
41. (b) T. Ishikawa, K. Nagai, T. Kudoh and S. Saito, Synlett, 1998, 1292.
42. M. P. Sibi, J. J. Shay, M. Liu and C. P. Jasperse, J. Am. Chem. Soc., 1998, 120, 6615.
43. (o) P. O'Brien, Angew. Chem., Int. Ed. Engl., 1998, 38, 326;
44. (b) L. J. Goossen, H. Liu, K. R. Dress and K. B. Sharpless, Angew. Chem., Int. Ed., 1999, 39, 1080 and references therein.
45. E. J. Corey, C. P. Decicco and R. C. Newbold, Tetrahedron Lett., 1991, 32, 5287.
46. K. Ishihara, M. Miyata, K. Hattori and H. Yamamoto, J. Am. Chem. Soc., 1994, 116, 10520.
47. For uses of differentially functionalized succinates in synthesis see: (a) M. P. Sibi, P. K. Deshpande and A. J. La Loggia, Synlett, 1996, 343;
48. (b) M. P. Sibi, J. Lu and C. L. Talbacka, J. Org. Chem., 1996, 61, 7848;
49. M. P. Sibi, J. Lu and J. Edwards, J. Org. Chem., 1997, 62, 5864.
50. For other selected methods for the synthesis of substituted succinates see: (a) C.-B. Xue, X. He, J. Roderick, W. F. DeGrado, R. J. Cherney, K. D. Hardman, D. J. Nelson, R. A. Copeland, B. D. Jatfee and C. P. Decicco, J. Med. Chem., 1998, 41, 1745;
51. (b) R. P. Becket, M. J. Crimmins, M. H. Davis and Z. A. Spavold, Synlett, 1993, 137.
52. G. Buchi and E. C. Robert, J. Org. Chcm., 1968, 33, 460.
53. G.-J. Ho and D. J. Mathre, J. Org. Chem., 1995, 60, 2271.
54. M. P. Sibi, P. K. Deshpande, A. J. La Loggia and J. W. Christensen, Tetrahedron Lett., 1995, 36, 8961.
55. For the use of this auxiliary see: (a) M. P. Sibi, C. P. Jasperse and J. Ji, J. Am. Chem. Soc., 1995, 117, 10779;
56. (b) M. P. Sibi and J. Ji, Angew. Chem., Int. Ed. Engl., 1996, 35, 190;
57. M. P. Sibi, P. K. Deshpande and J. Ji, Tetrahedron Lett., 1995, 36, 8965.
58. For selective aldol or alkylation of similar structural units see: (a) D. A. Evans and J. M. Takacs, Tetrahedron Lett., 1980, 21, 4233;
59. (b) D. A. Evans, M. D. Ennis and D. J. Mathre, J. Am. Chem. Soc., 1982, 104, 1737;
60. D. A. Evans, J. Bartroli and T. L. Shih, J. Am Chem. Soc., 1981, 103, 2127;
61. D. A. Evans, F. Urpi, T. C. Somer, J. S. Clark and M. T. Bilodeau, J. Am. Chem. Soc., 1990, 112, 8215;
62. (e) D. A. Evans, M. T. Bilodeau, T. C. Somer, J. Clardy, D. Cherry and Y. Kalo, J. Org. Chem., 1991, 56, 5750;
63. (f) W. Oppolzer, P. Cintas-Moreno, O. Tamura and F. Cardinaux, Helv. Chim. Acta, 1993, 76, 187.
64. (a) J. Weinstock, J. Org. Chem., 1961, 26, 3511;
65. (b) C. Kaiser and J. Weinstock, Org. Synth. 1988, coll. vol. 6, 910; The use of diphenylphosphoryl azide for the Curtius rearrangement gave lower yields and product purification was also difficult.
66. The diastereomers were purified by silica gel column chromatography. The two diastereomers from compound 7e were inseparable on column chromatography.
67. (a) J. M. Takacs, M. R. Jaber and A. S. Vellekoop, J. Org. Chem., 1998, 63, 2742;
68. (b) K. Burgess, D. Lim, K.-K. Ho and C.-Y. Ye, J. Org. Chem., 1994, 59, 2179;
69. (c) N. De Kimpe, M. Boeykens and K. A. Tehrani, J. Org. Chem., 1994, 59, 8215;
70. (d) F. Björkling, J. Boutelje, S. Gatenbeck, K. Hull and T. Norin, Tetrahedron Lett, 1985, 26, 4957;
71. (e) M. Martin-Vità, C. Minguillón and R. M. Ortuno, Tetrahedron: Asymmetry, 1995, 9, 4291.
72. The absolute stereochemistry of the alkylation product 7a was established by removal of both carboxy protecting groups to yield benzyl succinic acid and comparison of its sign of rotation with that reported in the literature (see Experimental section).
73. J. M. Bland, Synth. Commun., 1995, 25, 467 and references cited therein.
74. 26 + 5.33 (c 1.0, MeOH).
75. The acid 12e was purified to a single diastereomer by crystallization.
76. R. A. Barrow, T. Hemscheidt, J. Liane, S. Paik, R. E. Moore and M. A. Tius, J. Am. Chem. Soc., 1995, 117, 2479.
77. For recent work on cryptophycins and the synthesis of 14e see: J. D. White, J. Hong and L. A. Lobarge, J. Org. Chem. 1999, 64, 6206.
78. H. Kawano, Y. Ishii, T. Ikariya, M. Saburi, S. Yoshikawa, Y. Uchida and H. Kumobayashi, Tetrahedron Lett., 1987, 28, 1905.