CrIII(salen) catalysed asymmetric ring opening of monocyclic terpene-epoxides

Tetrahedron Letters

Volumn 44, Issue 25, 2003, Pages 4715-4717

  Dioos, Bart M L ^a   Jacobs, Pierre A ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM DERIVATIVE; EPOXIDE; TERPENE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; RING OPENING;

EID: 0037763977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01052-9     Document Type: Article

References (21)

1. Jacobsen E.N. Acc. Chem. Res. 33:2000;421-431.
2. Martinez L.E., Leighton J.L., Carsten D.H., Jacobsen E.N. J. Am. Chem. Soc. 117:1995;5897-5898.
3. Schaus S.E., Larrow J.F., Jacobsen E.N. J. Org. Chem. 62:1997;4197-4199.
4. Brandes B.D., Jacobsen E.N. Synlett. 2001;1013-1015.
5. Lebel H., Jacobsen E.N. Tetrahedron Lett. 40:1999;7303-7306.
6. Bauer K., Garbe D., Surburg H. Common Fragrance and Flavour Materials. Preparation, Properties and Uses. 1997;Wiley VCH, New York.
7. Comins D.L., Guerra-Weltzien L., Salvador J.M. Synlett. 11:1994;972-974 Bakthan, S.; William, C.; Goralski, C. (The Dow Chemical Company) WO Patent 02/22550 A2, 2002.
8. Comins D.L., Guerra-Weltzien L., Salvador J.M. Synlett. 11:1994;972-974 Bakthan, S.; William, C.; Goralski, C. (The Dow Chemical Company) WO Patent 02/22550 A2, 2002.
9. Chrisman W., Camara J.N., Marcellini K., Singaram B., Goralski C.T., Hasha D.L., Rudolf P.R., Nicholson L.W., Borodychuk K.K. Tetrahedron Lett. 42:2001;5805-5807.
10. Dreyfuss P., Kennedy J.P. Anal. Chem. 47:1975;771-774.
11. Venturello C., Alneri E., Ricci M. J. Org. Chem. 48:1983;3831-3833.
12. Kergomard A., Geneix M.Th. Bull. Soc. Chim. Fr. 1958;390-392.
13. Kergomard A., Geneix M.Th. Bull. Soc. Chim. Fr. 1958;394-396.
14. The catalyst is insoluble in noncoordinating solvents but readily soluble in donor solvents (ethereal solvents): Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. Soc. 1996, 118, 10924-10925.
15. All diastereomeric excesses were determined by chiral GC on a Chrompack-CHIRASIL-DEX CB column (0.32 mm×0.25 μm×25 m) using FID detection. The D.E.'s listed in Table 1 correspond to the composition of the reaction mixture and consequently do not reflect to the isolated products.
16. Keith J.M., Larrow J.F., Jacobsen E.N. Adv. Synth. Catal. 343:2001;5-26.
17. III(salen) catalyst.
18. 3 were removed from the reaction mixture by rotary evaporation. By adding a small amount of diethyl ether/hexane (5/95) to the residue, the catalyst precipitates and can easily be separated and recycled. The remaining mixture was purified by column chromatography (silica gel; diethyl ether/hexane: 5/95) and (-)-trans-limonene 1,2-epoxide (43% yield on epoxide, 89% D.E.) and azido product (36% yield, 90% D.E.) were recovered (not listed in Table 1). During the chromatographic work-up, desilylation of the azido compound already occurred due to the mild acidity of the silica combined with traces of water in the stationary phase.
19. Royals E.E., Leffingwell J.C. J. Org. Chem. 31:1966;1937-1944.
20. Larrow J.F., Schaus S.E., Jacobsen E.N. J. Am. Chem. Soc. 118:1996;7420-7421.
21. Schaus S.E., Larrow J.F., Jacobsen E.N. J. Org. Chem. 62:1997;4197-4199.