Enantioselective syntheses of α-substituted glutamic acids and α,γ-disubstituted glutamic acids by an asymmetric Strecker reaction

Tetrahedron Letters

Volumn 40, Issue 31, 1999, Pages 5753-5756

  Ma, Dawei ^a   Tang, Guozhi ^a   Tian, Hongqi ^a   Zou, Guixiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; GLUTAMIC ACID DERIVATIVE; GLYCINE DERIVATIVE; OXOACID; SODIUM DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; CRYSTAL STRUCTURE; HEATING; HYDROLYSIS; REDUCTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033618393     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01121-1     Document Type: Article

References (16)

1. For reviews, see Ma, D. Bioorganic Chemistry, 1999, 27, 20. Knopfel, T.; Kuhn, R.; Allgeier, H., J. Med.Chem. 1995, 38, 1418. Watkins, J. C.; Krogsgaard-Larsen, P.; Honore, T. Trends Pharmacol. Sci. 1990, 11, 25.
2. For reviews, see Ma, D. Bioorganic Chemistry, 1999, 27, 20. Knopfel, T.; Kuhn, R.; Allgeier, H., J. Med. Chem. 1995, 38, 1418. Watkins, J. C.; Krogsgaard-Larsen, P.; Honore, T. Trends Pharmacol. Sci. 1990, 11, 25.
3. For reviews, see Ma, D. Bioorganic Chemistry, 1999, 27, 20. Knopfel, T.; Kuhn, R.; Allgeier, H., J. Med.Chem. 1995, 38, 1418. Watkins, J. C.; Krogsgaard-Larsen, P.; Honore, T. Trends Pharmacol. Sci. 1990, 11, 25.
4. Jane, D. E.; Thomas, N. K.; Tse, H. W.; Watkins, J. C. Neuropharmacology, 1996, 35, 1029.
5. Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765.
6. Gu, Z.-Q.; Hessen, D.; Pelletier, J.; Maccechini, M.-L.; Zhou, L.-M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
7. Small, B.; Thomas, J.; Kemp. M.; Hoo, K.; Ballyk, B.; Deverill, M.; Ogden, A. M.; Rubio, A.; Pedregal, C.; Bleakman, D. Neuropharmacology, 1998, 37, 1261.
8. Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron:Asymmetry, 1998, 9, 3517.
9. a) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120;
10. b) Ma, D.; Ma, Z. Tetrahedron Lett. 1997, 38, 7599; and references cited therein.
11. Meyers, A. I.; Brengel, G. P. Chem Commun. 1997, 1, and references cited therein.
12. 3) δ 7.42-7.31 (m, 5H), 5.17 (dd, J = 10.8, 6.6 Hz, 1H), 4.62 (dd, J = 12.5, 6.7 Hz, 1H), 4.50 (dd, J = 12.4, 11.0 Hz, 1H), 2.71-2.52 (m, 2H), 2.44-2.26 (m, 2H), 2.08 (m, 1H), 1.94 (m, 1H), 1.05 (t, J = 7.3 Hz, 3H).
13. 3) δ 7.39-7.28 (m, 6H), 7.20-7.18 (m, 4H), 5.27 (dd, J = 11.4, 7.8 Hz, 1H), 4.70 (dd, J = 12.0, 7.8 Hz, 1H), 4.43 (dd, J = 12.6, 12.0 Hz, 1H), 3.08 (dd, J = 13.8, 4.2 Hz, 1H), 3.00 (dd, J = 13.2, 7.8 Hz, 1H), 2.98 (dd, J = 14.4, 11.4 Hz, 1H), 2.89-2.84 (m, 1H), 1.90 (m, 1H), 1.83 (dd, J = 13.5, 7.5 Hz, 1H), 1.32 (m, 1H), 0.83 (t, J = 7.2 Hz, 3H).
14. 2O) δ 2.39-2.31 (m, 2H), 2.09 (t, J = 7.6 Hz, 2H), 1.98 (dt, J = 14.7, 7.5 Hz, 1H), 1.88 (dt, J = 14.7, 7.3 Hz, 1H), 0.98 (t, J = 7.5 Hz, 3H).
15. Baussanne, I.; Royer, J. Tetrahedron Lett. 1998, 39, 845.
16. 2O) δ 7.33-7.25 (m, 2H), 7.23-7.20 (m, 3H), 2.84-2.67 (m, 2H), 2.53 (m, 1H), 1.96 (dd, J = 14.8, 9.1 Hz, 1H), 1.84 (dd, J = 14.8, 3.2 Hz, 1H), 1.31 (s, 3H).