Asymmetric synthesis of isoquinoline derivatives from amino acids

European Journal of Organic Chemistry

Volumn , Issue 4, 2005, Pages 663-672

  Sieck, Oxana ^a   Ehwald, Max ^a   Liebscher, Jürgen ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Amino acids; Asymmetric synthesis; Epoxidation; Heterocycles; Imidazoisoquinolinones

Indexed keywords

AMINO ACID; DIHYDROIMIDAZO[2,1 A]ISOQUINOLIN 3 ONE DERIVATIVE; DIMETHYLDIOXIRANE; ETHYLENE OXIDE DERIVATIVE; ISOQUINOLINE DERIVATIVE; MANDELIC ACID; TETRAHYDROIMIDAZO[2,1 A]ISOQUINOLIN 2 ONE DERIVATIVE; TETRAHYDROOXAZOLO[2,3 A]ISOQUINOLINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; COMPARATIVE STUDY; EPOXIDATION; HYDROGENATION; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 14944376421     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400693     Document Type: Article

References (29)

1. L. A. Carpino, E. M. E. Mansour, A. El-Faham, J. Org. Chem. 1993, 58, 4162.
2. L. A. Carpino, M. Beyermann, H. Wenschuh, M. Bienert, Acc. Chem. Res. 1996, 29, 268.
3. O. Sieck, S. Schaller, S. Grimme, J. Liebscher, Synlett 2003, 337.
4. O. Surygina, M. Ehwald, J. Liebscher, Tetrahedron Lett. 2000, 41, 5479.
5. H. Huys-Francotte, H. Bulli, Helv. Chim. Acta 1990, 73, 1679.
6. H. Tomoda, T. Hirano, S. Saito, T. Mutati, K. Araki, Bull. Chem. Soc. Jpn. 1999, 72, 1327.
7. H. Huys-Francotte, H. Bulli, Helv. Chim. Acta 1990, 73, 1679.
8. A. S. Howard, Comprehensive Heterocyclic Chemistry II, Elsevier Science, New York, 1996, vol. 8.
9. D. Beke, L. Toeke, Chem. Ber. 1962, 95, 2122.
10. S. Gunzenhauser, H. Balli, Helv. Chim. Acta 1985, 68, 56.
11. A. G. Burton, R. D. Frampton, C. D. Johnson, A. H. Katritzky, J. Chem. Soc., Perkin Trans. 2 1972, 1940.
12. Y. T. H. Shibuya, R. S. Zhang, R. X. Tong, I. Kiragawa, Chem. Pharm. Bull. 1992, 40, 2325.
13. A. Berger, E. Katchalski, J. Org. Chem. 1951, 16, 4084.
14. R. Müller, H. Goesmann, H. Waldmann, Angew. Chem. 1999, 111, 166.
15. Y. C. Hwang, M. F. Chu, W. Fowler, J. Org. Chem. 1985, 50, 3885.
16. B. Ronan, L. S. Hegedus, Tetrahedron Lett. 1993, 49, 5549.
17. T. Hamada, A. Nishida, Y. Matsumoto, O. Yonemitsu, J. Am. Chem. Soc. 1980, 102, 3978.
18. T. Hamada, A. Nishida, O. Yonemitsu, J. Am. Chem. Soc. 1986, 108, 140.
19. W. Adam, J. Bialas, L. Hadjiarapoglou, Chem. Ber. 1991, 124, 2377.
20. W. Adam, M. Ahrweiler, K. Paulini, H.-U. Reißig, V. Voerckel, Chem. Ber. 1992, 125, 2719.
21. S. M. Marcuccio, J. Elix, Austr. J. Chem. 1985, 38, 1785.
22. A. Bartels, P. G. Jones, J. Liebscher, Tetrahedron Lett. 1995, 36, 3673.
23. L. E. Burgess, E. K. M. Gross, J. Jurka, Tetrahedron Lett. 1996, 37, 3255.
24. S. G. Davies, M.-S. Key, H. Rodriguez-Solla, H. J. Sanganee, E. D. Savory, A. D. Smith, Synlett 2003, 1659.
25. L. A. Mitscher, H. Gill, J. A. Filppi, R. L. Wohlgemut, J. Med. Chem. 1986, 29, 1277.
26. K. T. Wanner, U. Weber, Synthesis 1994, 387.
27. U. Weber, K. T. Wanner, Z. Naturforsch., Teil B 1995, 50, 677.
28. E. Vedejs, C. Kongkittingam, J. Org. Chem. 2000, 65, 2309.
29. CCDC-250562, -250563 and -250564 contain the supplementary crystallographic data for for 5c, ent-17, and 7c. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.