Synthesis of optically active 2,3-substituted-1,2,3,4-tetrahydro-4- quinolones using polyleucine

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8495-8498

  Chen, Wei Ping ^a   Egar, Ann L ^b   Hursthouse, Michael B ^b   Malik, K M Abdul ^b   Mathews, Jude E ^a   Roberts, Stanley M ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 QUINOLONE DERIVATIVE; KETONE; LEUCINE;

EPOXIDATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; REVIEW; SYNTHESIS;

EID: 0032512029     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01249-0     Document Type: Article

References (17)

1. 1. Juliá, S.; Masana, J. and Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929.
2. 2. Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S. and Guixer, J. Tetrahedron, 1984, 40, 5207.
3. 3. Bentley, P.A.; Bergeron, S.; Cappi, M.W.; Hibbs, D.E.; Hursthouse, M.B.; Nugent, T.C.; Pulido, R.; Roberts, S.M. and Wu, L.E. Chem. Commun., 1997, 739.
4. 4. Bentley, P.A.; Kroutil, W.; Littlechild, J.A. and Roberts, S.M. Chirality, 1997, 9, 198.
5. 5. See Allen, J.V.; Cappi, M.W.; Kary, P.D.; Roberts, S.M.; Williamson, N.M. and Wu, L.E. J. Chem. Soc., Perkin Trans. 1, 1997, 3297 and references therein.
6. 6. Recent reviews of the area : Ebrahim, S. and Wills, M. Tetrahedron: Asymmetry, 1997, 8, 3163; Lasterra-Sánchez, M.E. and Roberts, S.M. Current Org. Chem., 1997, 1, 187.
7. 6. Recent reviews of the area : Ebrahim, S. and Wills, M. Tetrahedron: Asymmetry, 1997, 8, 3163; Lasterra-Sánchez, M.E. and Roberts, S.M. Current Org. Chem., 1997, 1, 187.
8. 7. de Diesbach, H. and Kramer, H. Helv. Chim. Acta, 1945, 28, 1399.
9. 8. Mannich, C. and Dannehl, M. Ber., 1938, 71, 1899; Janzso, G. and Philbin, E.M. Tetrahedron Lett., 1971, 3075; Gao, F.; Johnson, K.F. and Schlenoff, J.B. J. Chem. Soc., Perkin Trans. 2, 1996, 269.
10. 8. Mannich, C. and Dannehl, M. Ber., 1938, 71, 1899; Janzso, G. and Philbin, E.M. Tetrahedron Lett., 1971, 3075; Gao, F.; Johnson, K.F. and Schlenoff, J.B. J. Chem. Soc., Perkin Trans. 2, 1996, 269.
11. 8. Mannich, C. and Dannehl, M. Ber., 1938, 71, 1899; Janzso, G. and Philbin, E.M. Tetrahedron Lett., 1971, 3075; Gao, F.; Johnson, K.F. and Schlenoff, J.B. J. Chem. Soc., Perkin Trans. 2, 1996, 269.
12. 9. Donnelly, J.A. and Farrell, D.F. J. Org. Chem., 1990, 55, 1757.
13. 3) 64.8, 75.5, 115.7, 118.7, 127.9, 128.0, 128.9, 129.0, 136.2, 138.4, 151.5, 194.9.
14. 2=0.0943 for 1552 unique data and 215 parameters. Full details have been deposited with the Cambridge Crystallographic Data Centre.
15. 12. Adger, B.M.; Barkley, J.V.; Bergeron, S.; Cappi, M.W.; Flowerdew, B.E.; Jackson, M.P.; McCague, R.; Nugent, T.C. and Roberts, S.M. J. Chem. Soc., Perkin Trans. 1, 1997, 3501.
16. 13. Juliá, S.; Guixer, J.; Masana, J.; Rocas, J.; Colonna, S.; Annuziata, R. and Molinari, H. J. Chem. Soc., Perkin Trans. 1, 1982, 1317.
17. 14. cf. 4'-Hydroxychalcone, Dean, F.M. and Podimuang, V. J. Chem. Soc., 1965, 3978.