A short diastereoselective synthesis of orthogonally protected diaminosuccinic acid derivatives

Journal of Organic Chemistry

Volumn 69, Issue 18, 2004, Pages 6134-6136

  Zeitler, Kirsten ^a   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINOSUCCINIC ACIDS; DOUBLE BONDS;

CATALYSIS; CHEMICAL BONDS; DIMERS; HYDROGENATION; OLEFINS; SYNTHESIS (CHEMICAL);

ORGANIC ACIDS;

ALKENE; DIAMINO ACID; DIAMINOSUCCINIC ACID DERIVATIVE; GLYCINE; RHODIUM; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; HYDROGENATION; STEREOCHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

AMINO ACIDS, DIAMINO; CATALYSIS; GLYCINE; HYDROGENATION; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 4344632529     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049371e     Document Type: Article

References (57)

1. For comprehensive overviews of biologically active α,β-diamino acids, see: (a) Luo, Y.; Blaskovich, M. A.; Lajoie, G. A. J. Org. Chem. 1999, 64, 6106-6111.
2. (b) Dunn, P. J.; Häner, R.; Rapoport, H. J. Org. Chem. 1990, 55, 5017-5025 and references therein.
3. Most methodologies rely on stepwise preparations, often starting from chiral pool precursors. Recently, some new catalytic approaches such as olefinic diamination2a-c or Mannich reaction of imines with glycine derivatives2d have been developed: (a) Muñiz, K.; Nieger, B. Synlett 2003, 211-214.
4. (b) Pei, W.; Timmons, C.; Xu, X.; Wei, H.-X.; Li, G. Org. Biomol. Chem. 2003, 1, 2919-2921.
5. (c) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2003, 67, 4777-4781.
6. (d) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583-2591.
7. A summary of different synthetic methods and related literature can be found in ref la and (e) Ambroise, L.; Dumez, E.; Szeki, A.; Jackson, R. F. W. Synthesis 2002, 2296-2308.
8. (f) Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Flores, A.; Alonso, M. J. Org. Chem. 2004, 69, 1542-1547.
9. (a) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627.
10. (b) De Clercq, P. J. Chem. Rev. 1997, 97, 1755-1792 and references therein.
11. (a) Cox, R. J.; Sutherland, A.; Vederas, J. C. Bioorg. Med. Chem. 2000, 8, 843-871.
12. (b) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143.
13. (c) Roberts, J. L.; Chan, C. Tetrahedron Lett. 2002, 43, 7679-7682 and references therein.
14. (a) Williams, R. M.; Liu, J. J. Org. Chem. 1998, 63, 2130-2132.
15. (b) Nutt, R. F.; Strachan, R. G.; Veber, D. F.; Holly, F. W. J. Org. Chem. 1980, 45, 3078-3080.
16. (c) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815 and references therein.
17. Bhatnagar, P. K.; Agner, E. K.; Alberts, D.; Arbo, B. E.; Callahan, J. F.; Cuthbertson, A. S.; Engelsen, S. J.; Fjerdingstad, H.; Hartmann, M.; Heerding, D.; Hiebl, J.; Huffman, W. F.; Hysben, M.; King, A. G.; Kremminger, P.; Kwon, C.; LoCastro, S.; Løvhaug, D.; Pelus, L. M.; Petteway, S.; Takata, J. S. J. Med. Chem. 1996, 39, 3814-3819.
18. Diaminosuccinic acid (3-aminoaspartic acid)7a,c,d has been isolated from Streptomyces rimosus ((+)-(S,S)-diastereomer).7b Several studies support its possible use as ligand for aspartate-dependent enzymes that might be of interest for tumor therapy:7e (a) Ozaki, Y.; Iwasaki, T.; Miyoshi, M.; Matsumoto, K. J. Org. Chem. 1979, 44, 1714-1716.
19. (b) Hochstein, F. A. J. Org. Chem. 1959, 24, 679-680.
20. (c) McKennis, H.; Yard, A. S. J. Org. Chem. 1958, 23, 980-982.
21. (d) Biernat, J. F. Rocz. Chem. 1971, 45, 2081-2087.
22. (e) Chang, P. K.; Sciarini, L. J.; Handschumacher, R. E. J. Med. Chem. 1973, 16, 1277-1280.
23. Alvarez-Ibarra, C.; Csákÿ, A. G.; Colmenero, B.; Quiroga, M. L. J. Org. Chem. 1997, 62, 2478-2482.
24. Chen, Y.; Yudin, A. K. Tetrahedron Lett. 2003, 44, 4865-4868.
25. (a) Fernandez-Megia, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643-7652.
26. (b) Riemer, C.; Bayer, T.; Kessler, H. Peptides 1998, 25th European Peptide Symposium; Bajusz, S., Hudecz, F., Eds.; Akadémiai Kiadó: Budapest, 1999; pp 690-691.
27. Schumann, S.; Zeitler, K.; Jäger, M.; Polborn, K.; Steglich, W. Tetrahedron 2000, 56, 4187-4195.
28. (a) Ager, D. J. Curr. Opin. Drug Discov. Devel. 2002, 5, 892-905.
29. (b) Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103-151.
30. (c) Burk, M. J.; Bienewald, F. In Transition Metals in Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2, pp 13-24 and references therein.
31. As a consequence of the increasing interest in β-amino acids,13a several examples have been described; for a recent review, see ref 13b and references therein: (a) Gademann, K.; Hintermann, T.; Schreiber, J. V. Curr. Med. Chem. 1999, 6, 905-925.
32. (b) Drexler, H.-J.; You, J.; Zhang, S.; Fischer, C.; Baumann, W.; Spannenberg, A.; Heller, D. Org. Process Res. Dev. 2003, 7, 355-361.
33. Only few examples for the hydrogenation of diamino dehydroamino acid derivatives are known: (a) McGarrity, J.; Spindler, F.; Fuchs, R.; Eyer, M. European Patent EP-A 624 587A2, 1995; Chem. Abstr. 1995, 122, P81369q.
34. (b) Kuwano, R.; Okuda, S.; Ito, Y. Tetrahedron: Asymmetry 1998, 9, 2773-2775.
35. (c) Robinson, A. R.; Lim, C. Y.; He, L.; Ma, P.; Li, H.-Y. J. Org. Chem. 2001, 66, 4141-4147.
36. (d) Robinson, A. J.; Stanislawski, P.; Mulholland, D.; He, L.; Li, H.-Y. J. Org. Chem. 2001, 66, 4148-4152.
37. Hydrogenation of tetrasubstituted double bonds remains challenging; for some selected examples, see: (a) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376.
38. (b) Burk, M. J.; Gross, M. F.; Harper, G. P.; Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure Appl. Chem 1996, 68, 37-44.
39. In many cases the E- and Z-isomers show differences in respect to selectivity and conversion: (a) You, J.; Drexler, H.-J.; Zhang, S.; Fischer, C.; Heller, D. Angew. Chem., Int. Ed. 2003, 42, 913-916.
40. For cases in which only one enantiomer was obtained from an E/Z mixture, see: (b) Lee, S.; Zhang, Y. J. Org. Lett. 2002, 4, 2429-2431.
41. (c) Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159-4161 and references therein.
42. Most procedures have been developed for N-acyl protecting groups. Recently, successful approaches for N-carbamate-protected dehydroamino acids have been reported: (a) Evans, D. A.; Michael, F. E.; Tedrow, J. S.; Campos, K. R. J. Am. Chem. Soc. 2003, 125, 3534-3543.
43. (b) Burk, M. J. Acc. Chem. Res. 2000, 33, 363-372.
44. (c) Kuwano, R.; Ito, Y. J. Org. Chem. 1999, 64, 1232-1237.
45. (d) See ref 12c.
46. (e) Almena Perea, J. J.; Lotz, M.; Knochel, P. Tetrahedron: Asymmetry 1999, 10, 375-384.
47. 13C NMR spectra. Their stereochemical assignment was established by Sardina et al. by the analysis of NOE effects and coupling constants of their cyclic urea derivatives.10a
48. The low stereoselectivity might be due to isomerization processes on the catalyst's surface promoted by the long reaction times: King, A. O.; Larsen, R. D. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-VCH: Weinheim, 1998; Vol. 2, chapter VII.2, pp 13-24. This assumption is supported by the isolation of isomerized starting material (entry 1).
49. Because of the symmetry of starting material (Z)-3 syn addition of dihydrogen (as known from the model systems) at both sides of the double bond furnishes the same nonracemic diastereomer (anti)-4.
50. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1999.
51. (b) Clarke, P. A.; Martin, W. H. C. Annu. Rep. Prog. Chem., Sect. B 2003, 99, 84-103.
52. Several methods are known for deprotection of tert-butyl esters in the presence of Boc groups22a,b and vice versa.22c Selective cleavage of Cbz-protection is achievable via Pd-catalyzed hydrogenation; however, homogeneous hydrogenation leaves the Cbz group untouched.22d (a) Marcantoni, E.; Massaccesi, M.; Torregiani, E.; Bartoli, G.; Bosco, M.; Sambri, L. J. Org. Chem. 2001, 66, 4430-4432.
53. (b) Wu, Y.; Limburg, D. C.; Wilkinson, D. E.; Vaal, M. J.; Hamilton, G. S. Tetrahedron Lett. 2000, 41, 2847-2849.
54. (c) Gibson, F. S.; Bergmeier, S. C.; Rapoport, H. J. Org. Chem. 1994, 59, 3216-3218.
55. (d) Kreuzfeld, H.-J.; Döbler, C.; Krause, H. W.; Facklam, C. Tetrahedron: Asymmetry 1993, 4, 2047-2051.
56. For a general procedure for peptide dimerization see Supporting Information and ref 11.
57. After reaching an approximately 1:1 ratio of Z- and E-isomers, the reaction is terminated; non-converted Z-starting material can be recovered and reused.