The use of chiral auxiliaries prepared from (-)-β-pinene in stereoselective reduction of β-ketobutyrates

Synthetic Communications

Volumn 30, Issue 3, 2000, Pages 455-468

  Alencar, Karla G ^b   Filho, Ubiracir F ^b   Vasconcellos, Mário L A A ^a   Costa, Paulo R R ^a  

^a Nucleo de Pesq de Produtos Naturais   (Brazil)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYBUTYRIC ACID; ACETOACETIC ACID; BETA PINENE; BUTANEDIOL; CALCIUM CHLORIDE; MAGNESIUM CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0033955640     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910008087342     Document Type: Article

References (21)

1. Oppolzer, W. Tetrahedron 1987, 43, 1969. 2
2. (a)Corey, E.J. and Ensley, H.E. J.Am.Chem.Soc. 1975, 97, 6908.
3. (b) Chapman, B. J. and Jones, G. B. Synthesis 1995, 475.
4. Herzog, H., Scharf, H.D. Synthesis 1986, 420 and references cited therein.
5. (a)El Achaagar, THE., Boumzebra, M., Roumestant, M.L., Viallefont, P. Tetrahedron 1988, 44, 5319.
6. (b) Matterson, D. S. Chem. Rev. 1989, 89, 1535.
7. Solladie-Cavallo, T. and Koesseler, J.L. J.Org.Chem 1994, 59, 3240 and references cited therein.
8. Oppolzer, W., Kurth, M , Reichlin, D , Chapuis, C., Monhaupt, M., Moffart,F. Helv.Chim.Acta 1981, 64, 2802.
9. Vasconcellos,M.L.A.A., D'Angelo, J., Desmaele, D., Costa, P.R.R.and Potin, D. Tetrahedron:Asymmetry 1991, 2, 353.
10. Dumas, F., Mezrhab, B., D'Angelo, J. and Riche, C. J.Org.Chem. 1996, 61, 2293.
11. Dumas, F., Alencar,K., Mahuteau, J.; Barbero, M.J.L., Miet,C., Gérard, F., Vasconcellos, M.L.A.A and Costa, P.R.R. Tetrahedron:Asymmetry 1997, 8, 579.
12. Cabral, L.M., Costa ,P.R.R., Vasconcellos, M.L.A.A., Barreiro, E.J. and Castro,R.N. Synth. Commun. 1996, 26, 3671.
13. Costa, P.R.R., Cabrai, L.M., Alencar, K., Schmidt, L.L. and Vasconcellos, M.L.A.A. Tetrahedron Lett. 1997, 38, 7021
14. 10.(a)Fujii, H., Oshima, K. and Ultimoto, K. Chemistry Lett. 1992, 967.
15. (b) Fraga, C. A. M., Barreiro, E. J. Synth. Commun. 1995, 25, 1133.
16. Clemens, R.J. and Hyatt, J.A. J.Org.Chem 1985, 50, 2431.
17. 20= + 30 ( c = 1, EtOH), is commercially available from Aldrich Chemical Company.
18. Taber, D.F., Deker, P.B., Gaul, M. A. J.Am.Chem.Soc 1987, 109, 7488.
19. Maddaluno, J.F.; Gresh, N.; Giessner-Prettre, C.,J.Org.Chem. 1994, 59, 793.
20. Maddaluno, J.F; D'Angelo J.Am.Chem.Soc 1986, 108, 8112.
21. Hamon, D.P.G.; Holman, J.W.; Massy-Westropp, R.A .Tetrahedron 1993, 42, 9593.