(Salen) MnIII - Catalyzed Asymmetrie Epoxidation of Geraniol Derivatives

Synlett

Volumn 1996, Issue 11, 1996, Pages 1049-1050

  Garcia, Michel Ange ^a   Méou, Alain ^a   Brun, Pierre ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344919247     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5665     Document Type: Article

References (21)

1. Sharpless, K.B. Tetrahedron 1994, 50, 4235-4258.
2. Yamada, S.; Oh-hashi, N.; Achiwa, K. Tetrahedron Lett. 1976, 17, 2557-2560.
3. Meier, H.; Uebelhart, P.; Eugster, C.H. Helv. Chim. Acta 1986, 69, 106-123.
4. Eschenmoser, W.; Uebelhart, P.; Eugster, C.H. Helv. Chim. Acta 1983, 66, 82-91.
5. Aziz, M.; Rouessac, F. Tetrahedron 1988, 44, 101-110.
6. Chen, X.J.; Archelas, A.; Furstoss, R. J. Org. Chem. 1993, 58, 5528-5532.
7. Corey, E.J.; Noe, M.C.; Wen-Chung, S. Tetrahedron Lett. 1993, 34, 5995-5998.
8. a) Jacobsen, E.N. In Catalytic Asymmetrie Synthesis; Ojima, I., Ed.; V.C.H.: New York, 1993; pp 159-202.
9. b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214.
10. Brandes, B.D.; Jacobsen, E.N. J. Org. Chem. 1994, 59, 4378-4380.
11. Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198.
12. Jacobsen, E.N.; Zhang, W.; Muci, A.R.; Ecker, J.R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063-7064.
13. III catalysts for the oxidation of sulfides and the epoxidation of 2,2-dimethylchromenes, 1,2-dihydronaphthalene and trans β-methylstyrene: a) Palucki, M.; Jacobsen, E.N. Tetrahedron Leu. 1992, 33, 7111-7114. b) Schwenkreis, T.; Berkessel, A. Tetrahedron Lett. 1993, 34, 4785-4788. c) Irie, R.; Hosoya, N.; Katsuki, T. Synlett 1994, 255-256. d) Pietikäinen, P. Tetrahedron Lett. 1994, 35, 941-944.
14. III catalysts for the oxidation of sulfides and the epoxidation of 2,2-dimethylchromenes, 1,2-dihydronaphthalene and trans β-methylstyrene: a) Palucki, M.; Jacobsen, E.N. Tetrahedron Leu. 1992, 33, 7111-7114. b) Schwenkreis, T.; Berkessel, A. Tetrahedron Lett. 1993, 34, 4785-4788. c) Irie, R.; Hosoya, N.; Katsuki, T. Synlett 1994, 255-256. d) Pietikäinen, P. Tetrahedron Lett. 1994, 35, 941-944.
15. III catalysts for the oxidation of sulfides and the epoxidation of 2,2-dimethylchromenes, 1,2-dihydronaphthalene and trans β-methylstyrene: a) Palucki, M.; Jacobsen, E.N. Tetrahedron Leu. 1992, 33, 7111-7114. b) Schwenkreis, T.; Berkessel, A. Tetrahedron Lett. 1993, 34, 4785-4788. c) Irie, R.; Hosoya, N.; Katsuki, T. Synlett 1994, 255-256. d) Pietikäinen, P. Tetrahedron Lett. 1994, 35, 941-944.
16. III catalysts for the oxidation of sulfides and the epoxidation of 2,2-dimethylchromenes, 1,2-dihydronaphthalene and trans β-methylstyrene: a) Palucki, M.; Jacobsen, E.N. Tetrahedron Leu. 1992, 33, 7111-7114. b) Schwenkreis, T.; Berkessel, A. Tetrahedron Lett. 1993, 34, 4785-4788. c) Irie, R.; Hosoya, N.; Katsuki, T. Synlett 1994, 255-256. d) Pietikäinen, P. Tetrahedron Lett. 1994, 35, 941-944.
17. 2O from 96/4 to 80/20).
18. det.: 250°C; isotherm: 110°C. Retention times: 26.3 min for the (65)-isomer and 27.1 min for the (6R)-isomer.
19. Eliel, E.L.; Wilen, S.H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 216-221 and 249-253.
20. Larrow, J.F.; Jacobsen, E.N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C.M.J. Org. Chem. 1994, 59, 1939-1942.
21. Donike, M. J. Chromatogr. 1973, 78, 273-279.