Efficient synthesis of 2-aminoindane-2-carboxylic acid via dialkylation of nucleophilic glycine equivalent

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4973-4976

  Ellis, Trevor K ^a   Hochla, Veronica M ^a   Soloshonok, Vadim A ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL YIELD;

ALKYLATION; COMPLEXATION; DECOMPOSITION; PHASE TRANSITIONS;

CARBOXYLIC ACIDS;

2 [N (ALPHA PICOLYL)AMINO]BENZOPHENONE; 2 AMINOINDANE 2 CARBOXYLIC ACID; 2 DIBROMOXYLYLENE; BENZOPHENONE DERIVATIVE; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; GLYCINE DERIVATIVE; INDAN DERIVATIVE; LIGAND; N,N DIMETHYLFORMAMIDE; NICKEL COMPLEX; SCHIFF BASE; UNCLASSIFIED DRUG;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; COMPLEX FORMATION; CYCLIZATION; DECOMPOSITION; PHASE TRANSITION; PURIFICATION; REACTION ANALYSIS;

ALKYLATION; AMINO ACIDS; CARBOXYLIC ACIDS; CATALYSIS; CYCLIZATION; GLYCINE; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 0038277395     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030065v     Document Type: Article

References (37)

1. For a recent collection of leading research papers on sterically constrained amino acids, see: Hruby, V. J., Soloshonok, V. A., Guest Editors. Asymmetric Synthesis of Novel Sterically Constrained Amino Acids; Tetrahedron Symposia-in-Print, No. 88. In Tetrahedron 2001, 57(30).
2. For a review on topographical, 3D characteristics of sterically constrained amino acids, see: Gibson, S. E.; Guillo, N.; Tozer, M. J. Tetrahedron 1999, 55, 585.
3. (a) Hruby, V. J. Life Sci. 1982, 31, 189.
4. (b) Hruby, V. J.; AlObeidi, F.; Kazmierski, W. M. Biochem. J. 1990, 268, 249.
5. (c) Hruby, V. J. Biopolymers 1993, 33, 1073.
6. (d) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. D. Biopolymers 1997, 43, 219.
7. (a) Pinder, R. M.; Butcher, B. H.; Buxton, D. A.; Howells, D. J. J. Med. Chem. 1971, 14, 892.
8. (b) Hsieh, K.; Jorgensen, E. C. J. Med. Chem. 1979, 22, 1038.
9. (c) Gavuzzo, E.; Lucente, G.; Mazza, F.; Pagani-Zecchini, G.; Paglialunga-Paradisi, M.; Pochetti, G.; Torrini, I. Int. J. Peptide Protein Res. 1991, 37, 268.
10. (d) Schiller, P. W.; Weltrowska, G.; Nguyen, T. M.-D.; Lemieux, C.; Chung, N. N.; Marsden, B. J.; Wilkes, B. C. J. Med. Chem. 1991, 34, 3125.
11. (e) Mendel, D.; Ellman, J.; Schultz, P. G. J. Am. Chem. Soc. 1993, 115, 4359.
12. (f) Leftheris, K.; Kline, T.; Vite, G. D.; Cho, Y. H.; Bhide, R. S.; Patel, D. V.; Patel, M. M.; Schmidt, R. J.; Weller, H. N.; Andahazy, M. L.; Carboni, J. M.; Gullo-Brown, J. L.; Lee, F. Y. F.; Ricca, C.; Rose, W. C.; Yan, N.; Barbacid, M.; Hunt, J. T.; Meyers, C. A.; Seizinger, B. R.; Zahler, R.; Manne, V. J. Med. Chem. 1996, 39, 224.
13. (g) Lecaille, F.; Authié, E.; Moreau, T.; Serveau, C.; Gauthier, F.; Lalmanach, G. Eur. J. Biochem. 2001, 268, 2733.
14. (a) Williams, L. J.; Jagadish, B.; Lansdown, M. G.; Carducci, M. D.; Mash, E. A. Tetrahedron 1999, 55, 143012.
15. (b) Williams, L. J.; Jagadish, B.; Lyon, S. R.; Kloster, R. A.; Carducci, M. D.; Mash, E. A. Tetrahedron 1999, 55, 14281-14300.
16. Palacin, S.; Chin, D. N.; Simanek, E. E.; MacDonald, J. C.; Whitesides, G. M.; McBride, M. T.; Palmore, G. T. R. J. Am. Chem. Soc. 1997, 119, 11807.
17. (a) Pinder, R. M.; Butcher, B. H.; Buxton, D. A.; Howells, D. J. J. Med. Chem. 1971, 14, 892.
18. (b) Avindano, C.; Trigo, G. G. The Chemistry of Hydantoins. In Advances in Heterocyclic Chemistry; Academic Press: New York, 1985; Vol. 38, p 177.
19. (c) Zon, J.; Amrhein, N. Liebig Ann. 1992, 6, 625.
20. (d) Francescheti, L.; Agurbeh, A. G.; Mahmoud, M. R.; Natalini, B.; Pelliceiari Tetrahedron Lett. 1993, 34, 3185.
21. (e) Fatino, G.; Fogagnolo, M.; Guenini, R.; Marastoni, M.; Medici, A.; Pedrini, P. Tetrahedron 1994, 53, 12973.
22. (f) Ezquerra, J.; Yruretagoyena, B.; Avendano, C.; de la Cuesta, E.; Gonzalez, R.; Prieto, L.; Pedregal, C.; Espada, M.; Prowse, W. Tetrahedron 1995, 54, 3271.
23. (g) Tellier, F.; Acher, F.; Brabet, I.; Pin, J.-P.; Azerad, R. Bioorg. Med. Chem. 1998, 6, 195.
24. (h) Baker, S. R.; Hancox, T. C. Tetrahedron Lett. 1999, 40, 781.
25. (i) Kubik, S.; Meissner, R. S.; Rebeck, J., Jr. Terahedron Lett. 1994, 35, 6635.
26. Kotha, S.; Brahmachary, E. J. Org. Chem. 2000, 65, 1359.
27. Ellis, T. K.; Martin, C. H.; Ueki, H.; Soloshonok, V. A. Tetrahedron Lett. 2003, 44, 1063.
28. Lygo, B. Tetrahedron 2001, 57, 6447.
29. For the recently developed efficient, large-scale synthesis of Ni-(II) complexes 2a,b, see: Ueki, H.; Ellis, T. K.; Collin, M. H.; Soloshonok, V. A. Eur. J. Org. Chem. 2003, in press.
30. Ligand PAAP and complex 2a were introduced by our group: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Org. Lett. 2000, 2, 747. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Yamazaki, T. J. Org. Chem. 2000, 65, 6688.
31. Ligand PAAP and complex 2a were introduced by our group: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Org. Lett. 2000, 2, 747. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Yamazaki, T. J. Org. Chem. 2000, 65, 6688.
32. Ligand PAAP and complex 2b were introduced by Belokon's group: Belokon, Y. N., Koehetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Larionov, O. V.; Harutyunyan, S. R.; Vyskocil, S.; North, M.; Kagan, H. B. Angew. Chem., Int. Ed. 2001, 40, 1948.
33. (a) Stork, G.; Leong, A. Y. W.; Touzin, A. M. J. Org. Chem. 1976, 41, 3491.
34. (b) O'Donnell, M.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
35. (a) Soloshonok, V. A. Curr. Org. Chem. 2002, 6, 341.
36. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135.
37. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 9645.