Epoxidation of electron deficient alkenes using tert-butyl hydroperoxide and 1,5,7-triazabicyclo[4.4,0]dec-5-ene and its Derivatives

Synlett

Volumn , Issue 6, 1999, Pages 795-797

  Genski, Thorsten ^a   Macdonald, Gregor ^a   Wei, Xudong ^a   Lewis, Norman ^b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Alkenes; Epoxidation; Guanidine

Indexed keywords

ALKENE DERIVATIVE; BENZOQUINONE DERIVATIVE; GUANIDINE DERIVATIVE; KETONE DERIVATIVE; NAPHTHOQUINONE; QUINONE DERIVATIVE; TERT BUTYL HYDROPEROXIDE;

ARTICLE; ENANTIOMER; EPOXIDATION; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 0033056178     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2721     Document Type: Article

References (20)

1. Meth-Cohn, O.; Moore, C.; Taljaard, H. C. J. Chem. Soc., Perkin Trans. J 1988, 2663 and references therein.
2. Schlessinger, R. H.; Bebernitz, G. R.; Lin, P.; Poss, A. J. J. Am. Chem. Soc. 1985, 107, 1777;
3. Yadav, V. K.; Kapoor, K. K. Tetrahedron 1995, 51, 8573.
4. For other aprotic epoxidation procedures see references 1, 2 and: Yadav, V. K.; Kapoor, K. K. Tetrahedron Lett. 1994, 35, 9481;
5. Still, W. C. J. Am. Chem. Soc. 1979, 101, 2493 and references therein.
6. Taylor, R. J. K.; Alcaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775;
7. Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. J. Org. Chem. 1998, 63, 3526.
8. McKay, A. F.; Kreling, M.-E. Can. J. Chem. 1957, 35, 1438.
9. Raczynska, E. D.; Maria, P.-C.; Gal, J.-F.; Decouzon, M. J. Phys. Org. Chem. 1994, 7, 725 and references cited therein.
10. Horváth, A. Tetrahedron Lett. 1996, 37, 4423.
11. Alcázar, V.; Morán, J. R.; de Mendoza, J. Tetrahedron Lett. 1995, 56, 3941.
12. Alder, R. W.; Mowlam, R. W.; Vachon, D. J.; Weisman, G. R. Chem. Commun. 1992, 507; see also reference 11.
13. Subba Rao, Y.V.; De Vos, D.E.; Jacobs, P. A. Angew. Chem. Int. Ed. Engl. 1997, 36, 2661.
14. Ragot, J. P.; Steeneck, C.; Alcaraz, M.-L.; Taylor, R. J. K. Taylor J. Chem. Soc., Perkin Trans. I 1999, 1073.
15. Kosasayama, A.; Konno, T.; Higashi, K.; Ishikawa, F. Chem. Pharm. Bull. 1979, 27, 841; we prepared 4c directly by alkylation of 4a with benzhydryl bromide.
16. 13C NMR spectroscopy and by elemental analysis or high resolution mass spectrometry.
17. 4d-f were prepared from 4a by reaction with the corresponding epoxide; 4g was prepared by deprotonation of 4b and trapping with camphor.
18. Macdonald, G.; Alcaraz, L.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 5433.
19. 17 95-98 °C) with consistent spectroscopic data.
20. Jackson-Mülly, M.; Zsindely, J.; Schmid, H. Helv. Chim. Acta 1976, 59, 664.