Asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylenedimerization of chiral glycine equivalents with dichloromethane under operationally convenient conditions

Tetrahedron Letters

Volumn 45, Issue 50, 2004, Pages 9159-9162

  Taylor, Stephen M ^a   Yamada, Takeshi ^a   Ueki, Hisanori ^a   Soloshonok, Vadim A ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

4 Aminoglutamic acids; Asymmetric synthesis; Bis amino acids; Methylenedimerization

Indexed keywords

BROMINE DERIVATIVE; DICHLOROMETHANE; GLUTAMIC ACID DERIVATIVE; GLYCINE; NICKEL COMPLEX; SCHIFF BASE; SODIUM HYDROXIDE;

AQUEOUS SOLUTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; DIMERIZATION; ENANTIOMER; ROOM TEMPERATURE;

EID: 8544228333     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.111     Document Type: Article

References (25)

1. R.J. Cox Nat. Prod. Rep. 15 1998 279
2. J.B. Ward Pharmac. Ther. 25 1984 327 and references cited therein
3. V.A. Soloshonok Current Org. Chem. 6 2002 341
4. V.A. Soloshonok, C. Cai, and V.J. Hruby Tetrahedron Lett. 41 2000 135
5. V.A. Soloshonok, C. Cai, V.J. Hruby, L.V. Meervelt, and T. Yamazaki J. Org. Chem. 65 2000 6688
6. V.A. Soloshonok, C. Cai, and V.J. Hruby Org. Lett. 2 2000 747
7. V.A. Soloshonok, C. Cai, and V.J. Hruby Angew. Chem., Int. Ed. 39 2000 2172
8. V.A. Soloshonok, C. Cai, and V.J. Hruby Tetrahedron Lett. 41 2000 9645
9. C. Cai, V.A. Soloshonok, and V.J. Hruby J. Org. Chem. 66 2001 1339
10. V.A. Soloshonok, H. Ueki, R. Tiwari, C. Cai, and V.J. Hruby J. Org. Chem. 69 2004 4984
11. J. Folbergrova, R. Haugvicova, and P. Mares Bioorg. Med. Chem. Lett. 11 2001 1919
12. N. Jullian, I. Brabet, J. Pin, and F.C. Acher Bioorg. Med. Chem. Lett. 9 1999 1721
13. G. Kostantino, A. Macchiarulo, and R. Pellicciari J. Med. Chem. 42 1999 1546
14. I. Panfil, Z. Urbanczyk-Lipkowska, K. Suwinska, J. Solecka, and M. Chmielewski J. Med. Chem. 42 1999 2816
15. P. Conti, M. De Amici, G. De Sarro, T.B. Stensbol, H. Braeuner-Osborne, U. Madsen, and C. De Micheli J. Med. Chem. 42 1999 2816
16. K. Tanaka, and H. Sawanishi Tetrahedron: Asymmetry 9 1998 71
17. A. Avenoza, C. Cativiela, J.M. Peregrina, and M.M. Zurbano Tetrahedron: Asymmetry 7 1996 1555
18. A. Avenoza, C. Cativiela, J.M. Peregrina, and M.M. Zurbano Tetrahedron: Asymmetry 8 1997 863
19. Y. Arakawa, T. Goto, K. Kawase, and S. Yoshifuji Chem. Pharm. Bull. 43 1995 535
20. Y. Arakawa, T. Goto, K. Kawase, and S. Yoshifuji Chem. Pharm. Bull. 46 1998 674
21. V.P. Krasnov, E.A. Zhdanova, M.A. Korolyova, I.M. Bukrina, M.I. Kodess, V.K. Kravtsov, and V.N. Biyushkin Russ. Chem. Bull. 46 1997 319
22. M.M. Kabat Tetrahedron Lett. 42 2001 7521
23. L. Eberson Acta Chem. Scand. 12 1958 314
24. Y.N. Belokon, N.I. Chernoglazova, A.S. Batsanov, N.S. Garbalinskaya, V.I. Bakhmutov, Y.T. Struchkov, and V.M. Belikov Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 4 1987 852
25. Complete details of our experiments aimed to improve preparation of product 3 under acetonitrile/NaOH (Belokon's) conditions will be reported in the full publication on this project