Dynamic kinetic resolution of acyclic allylic acetates using lipase and palladium

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8423-8424

  Choi, Yoon Kyung ^a   Suh, Jong Hwa ^a   Lee, Donghyun ^a   Lim, In Taek ^a   Jung, Jae Yoon ^a   Kim, Mahn Joo ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; PALLADIUM COMPLEX; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOMER; ENZYME KINETICS; ESTERIFICATION; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0000419728     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990956w     Document Type: Article

References (19)

1. Undergraduate research participant.
2. Strauss, U. T.; Felfer, U.; Faber, K. Tetrahedron: Asymmetry 1999, 10, 107.
3. Review on dynamic kinetic resolution: Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475.
4. Previous reports: (a) Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859.
5. (b) Dinh, P. M.; Howarth, J. A.; Hudnott, A. R.; Williams, J. M. J.; Harris, W. Tetrahedron Lett. 1996, 37, 7623-26.
6. Reetz, M. T.; Schimossek, K. Chimia 1996, 50, 668.
7. Persson, B. A.; Larsson, A. L. E.; Ray, M. L.; Bäckvall, J.-E. J. Am. Chem. Soc. 1999, 121, 1645.
8. PCL immobilized on ceramic particles (trade name, Lipase PS-C (type II), Amano, Japan) and CAL immobilized on acrylic resin (trade name, Novozym 435, Novo Nordisk Korea) were used.
9. Most likely this racemization proceeds via cis-migration of coordinated acetate in the intermediate (π-allyl)palladium complex ( Trost. B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron Lett. 1979, 130.
10. Bäckvall, J. E.; Nordberg, R. E.; Björkman, E. E.; Moberg, C. J. Chem. Soc., Chem. Commun. 1980, 943.
11. Bäckvall, J. E.; Nordberg, R. E.; Wilhelm, D. J. Am. Chem. Soc. 1985, 107, 6892).
12. It may also proceed via a Pd-to-Pd displacement (Granberg, K. L.; Bäkvall, J. E. J. Am. Chem. Soc. 1992, 114, 6858).
13. 4.
14. (a) Södergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760.
15. (b) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. J. Am. Chem. Soc. 1998, 720, 13529.
16. (a) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 4, p 585.
17. (b) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 827.
18. Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, Vol. 7, p 389.
19. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.