Comments on an attempted synthesis of 1-aminocyclopropane-1,2-dicarboxylic acid

Synthetic Communications

Volumn 26, Issue 5, 1996, Pages 1041-1049

  Taylor, Edward C ^a   Hu, Baihua ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 1,2 CYCLOPROPANE DICARBOXYLIC ACID; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029899216     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003709     Document Type: Article

References (12)

1. For reviews on cyclopropyl amino acids see: (a) Salaun, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511 (b) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett, 1994, 575 (c) Alami, A.; Calmes, M; Daunis, J. and Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5
2. For reviews on cyclopropyl amino acids see: (a) Salaun, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511 (b) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett, 1994, 575 (c) Alami, A.; Calmes, M; Daunis, J. and Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5
3. For reviews on cyclopropyl amino acids see: (a) Salaun, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511 (b) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett, 1994, 575 (c) Alami, A.; Calmes, M; Daunis, J. and Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5
4. (d) Stammer, C. H. Tetrahedron 1990, 46, 2231
5. (e) Vilsmaier, E. in "The Chemistry of the Cyclopropyl Group"; Rappoport, Z. Ed.; John Wiley & Sons Ltd.; New York, 1987, 1341.
6. For recent discussions of the potential importance of such glutamic acid mimics, see: (a) Knopfel, T.; Kuhn, R. and Allgeier, H. J. Med. Chem. 1995, 38, 1417 (b) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277.
7. For recent discussions of the potential importance of such glutamic acid mimics, see: (a) Knopfel, T.; Kuhn, R. and Allgeier, H. J. Med. Chem. 1995, 38, 1417 (b) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277.
8. Kraus, G. A.; Kim, H.; Thomas, P. J.; Metzler, D. E.; Metzler, C. M.; Taylor, J. E. Synth. Commun. 1990, 20, 2667.
9. McDonald, R. N.; Reitz, R. R. J. Org. Chem. 1972, 37, 2418.
10. 4) δ 3.73 (s, 3 H), 3.66 (s, 3 H), 3.43 (s, 3 H), 2.25 (dd, J = 10.1, 8.1 Hz, 1 H), 1.85 (dd, 7 = 8.1, 5.9 Hz, 1 H), 1.49 (dd, J= 10.1, 5.9 Hz, 1 H).
11. +): calcd 188.0685; found 188.0697.
12. Kakimoto, M.; Kai, M.; Kondo, K. Chem. Lett. 1982, 525.