Asymmetric epoxidation of allylic alcohols catalyzed by new chiral vanadium(V) complexes

Tetrahedron Asymmetry

Volumn 13, Issue 24, 2002, Pages 2625-2628

  Wu, Hsyueh Liang ^a   Uang, Biing Jiun ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALCOHOL DERIVATIVE; BORNANE DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; KETOPINIC ACID; LIGAND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHIRALITY; EPOXIDATION; PRIORITY JOURNAL;

EID: 0037049386     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00741-3     Document Type: Article

References (23)

1. Behrens C.H., Sharpless K.B. Aldrichim. Acta. 16:1983;67.
2. Rao A.S. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 7:1991;357 Pergamon, Oxford.
3. Jacobsen E.N. Ojima I. Catalytic Asymmetric Synthesis. 1993;159 VCH, New York.
4. Katsuki T. Coord. Chem. Rev. 140:1995;189.
5. Katsuki T. J. Mol. Catal. 113:1996;87.
6. Dalton C.T., Ryan K.M., Wall V.M., Bousquet C.D., Gilheany G. Top. Catal. 5:1998;75.
7. Muñiz-Fernández K., Bolm C. Beller M., Bolm C. Transition Metals for Organic Synthesis. 2:2000;271 VCH-Wiley, Weinheim.
8. Katsuki T. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. 2:1999;621 Springer, Berlin.
9. Ito Y.N., Katsuki T. Bull. Chem. Soc. Jpn. 72:1999;603.
10. Michaelson R.C., Palermo R.E., Sharpless K.B. J. Am. Chem. Soc. 99:1977;1990.
11. Vanadium complex bearing proline-based chiral hydroxamic acid provided 80% ee, see: Sharpless K.B., Verhoeven T.R. Aldrichim. Acta. 12:1979;63.
12. Murase N., Hoshino Y., Oishi M., Yamamoto H. J. Org. Chem. 64:1999;338.
13. Luong T.K.K., Harms K., Bolm C. Chem Ber./Recl. 130:1997;887.
14. Kühn T., Bolm C. Synlett. 6:2000;899.
15. More recently chiral hydroperoxides were used as oxidant in asymmetric oxidations, see: Bolm C., Beckmann O., Kühn T., Palazzi C., Adam W., Rao P.B., Saha-Möller C.R. Tetrahedron: Asymmetry. 12:2001;2441.
16. Hoshino Y., Yamamoto H. J. Am. Chem. Soc. 122:2000;10452.
17. Hwang D.-R., Chu C.-Y., Wang S.-K., Uang B.-J. Synlett. 1:1999;77.
18. Hwang D.-R., Chen C.-P., Uang B.-J. Chem. Commun. 1999;1207.
19. Chu C.-Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980.
20. Hwang D.-R., Uang B.-J. Org. Lett. 4:2002;463.
21. iPrOH=98:2; flow rate: 1 ml/min).
22. 2a.
23. 2a.