Reinvestigation of the alkylation of pyroglutamate ester urethanes

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2199-2202

  Charrier, Jean Damien ^a   Duffy, James E S ^a   Hitchcock, Peter B ^a   Young, Douglas W ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYROGLUTAMIC ACID DERIVATIVE; URETHAN DERIVATIVE;

ALKYLATION; ARTICLE; CHELATION; CHIRALITY; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PROTEIN CONFORMATION; RELIABILITY; STEREOCHEMISTRY;

EID: 0032499038     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00174-9     Document Type: Article

References (21)

1. 1. Baldwin, J. E.; Miranda, T.; Moloney, M.; Hokelek, T., Tetrahedron, 1989, 45, 7459-7468.
2. 2. Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Escribano, A.; Sanchez-Ferrando, F., Tetrahedron, 1993, 49, 8665-8678.
3. 3. Ostler, G.; Soteriou, A.; Moody, C. M.; Khan, J. A.; Birdsall, B.; Carr, M. D.; Young, D. W.; Feeney, J., FEBS. Lett., 1993, 318, 177-180.
4. 4. (a) August, R. A.; Khan, J. A.; Moody, C. M.; Young, D. W., Tetrahedron Lett., 1992, 33, 4617-4620;
5. (b) ibid., J. Chem. Soc., Perkin Trans. 1, 1996, 507-514.
6. 5. (a) Moody, C. M.; Young, D. W., Tetrahedron Lett., 1993, 34, 4667-4670;
7. (b) ibid., Tetrahedron Lett., 1994, 35, 7277-7280;
8. (c) ibid, J. Chem. Soc., Perkin Trans. 1, 1997, 3519-3530.
9. 6. Moody, C. M.;. Starkmann, B. A.; Young, D. W., Tetrahedron Lett., 1994, 35, 5485-5488.
10. 7. (a) Feeney, J.; McCormick, J. E.; Bauer, C. J.; Birdsall, B.; Moody, C. M.; Starkmann, B. A.; Young, D. W.; Francis, P.; Havlin, R. H.; Arnold, W. D.; Oldfield, E., J. Am. Chem. Soc., 1996, 118, 8700-8706;
11. (b) ibid, idem, supplementary material.
12. 2 using SHELXL-93 with non-H atoms anisotropic and H atoms in riding mode. Final residuals were R1 = 0.049 (for 1171 reflections with I>2σ(I)) and wR2 = 0.125 (for all reflections). The atomic coordinates are available on request from The Director, Cambridge Crystallography Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW.
13. 9. Langlois, N.; Rojas, A., Tetrahedron Lett., 1993, 34, 2477-2480.
14. 2
15. 11. Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F., J. Amer. Chem. Soc., 1997, 119, 4565-4566.
16. 12. Meyers, A. I., Accounts of Chem. Res., 1978, 11, 375-381.
17. 13. Laube, T.; Dunitz, J. D.; Seebach, D., Helv. Chim. Acta, 1985, 68, 1373-1393.
18. 14. Armstrong, R. W.; DeMattei, J. A., Tetrahedron Lett., 1991, 32, 5749-5752.
19. 15. Seebach, D., Angew. Chem., Int. Ed. Engl., 1988, 27, 1624-1654.
20. 16. Davies, S. G.; Garrido, N. M.; Ichihara, O.; Walters, I. A. S., J. Chem. Soc., Chem. Commun., 1993, 1153-1155.
21. 17. Hanessian, S.; Reinhold, U.; Gentile, G., Angew. Chem., Int. Edn. Engl., 1997, 36, 1881-1884.