Asymmetric catalysis by a chiral ruthenium porphyrin: Epoxidation, hydroxylation, and partial kinetic resolution of hydrocarbons

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2077-2080

  Gross, Zeev ^a   Ini, Santiago ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000042473     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991131b     Document Type: Article

References (26)

1. Groves, J. T.; Myers. R. S.J. Am. Chem. Soc. 1983, 105, 5791.
2. Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E.; Brauman, J. I. Science 1993, 261, 1404 and references therein.
3. Ini, S.; Kapon, M.; Cohen, S.; Gross, Z. Tetrahedron: Asymmetry 1996, 7, 659.
4. Gross, Z.; Ini, S.; Kapon, M.; Cohen S. Tetrahedron Lett. 1996, 37, 7325.
5. Berkessel, A.; Frauenkron, M. J. Chem. Soc., Perkin Trans, 1 1997, 2265.
6. Lai. T.-S.; Kwong, H.-L.; Zhang, R.; Che. C.-M. J. Chem. Soc., Dalton Trans. 1998, 3559.
7. (a) Gross, Z.; Galili, N.; Simkhovich, L. Tetrahedron Lett. 1999, 40, 1571.
8. (b) Galardon, E.; Roue, S.; Le Maux, P.; Simonneaux, G. Tetrahedron Lett. 1998, 39, 2333.
9. (c) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175.
10. (d) Lo, W.-C.; Che, C-M.; Cheng, K.-F.; Mak, T. C. W. J. Chem. Soc., Chem. Commun. 1997, 1205.
11. (e) Galardon, E.; Le Maux, P.; Simonneaux. G. J. Chem. Soc.. Chem. Commun. 1997, 927.
12. O'Malley, S.; Kodadek, T. Organometallics 1992, 11, 2299.
13. Gross, Z.; Ini, S. J. Org. Chem. 1997, 62, 5514.
14. Gross, Z.; Ini, S. Inorg. Chem. 1999, 38, 1446.
15. Halterman, R. L.; Jan, S.-T.; Nimmons, H. L.; Standlee, D. J.; Khan, M. A. Tedrahedron 1997, 53, 11257.
16. Katsuki, T. J. Mol. Catal. A 1996, 113, 87
17. Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che. C.-M. J. Chem. Soc., Chem. Commun. 1999, 409.
18. The full synthetic procedures are provided as Supporting Information.
19. Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
20. Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692.
21. End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem. Eur. J. 1998, 4, 818 and references therein.
22. (a) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
23. (b) Without HX the reaction is much less efficient, a phenomenon under current investigation in our laboratory.
24. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless. K. B. J. Am. Chem. Soc. 1981, 103, 6237.
25. Reactions conditions: 24 h at O °C with 0.1 μmol of catalyst, 25 μmol of oxidant, 50 μmol of alkane, and 5 μL of a HCl-saturated benzene solution in 0.5 mL of chlorobenzene under Ar. Chemical yields were determined by GC analysis relative to an internal standard. Enantiomeric excesses were determined by GC, using a Cyclodex-B chiral capillary column for the alcohol and Chiraldex A-TA for the alkane.
26. Takeda, T.; Irie, R.; Katsuki, T. Svnlett 1999, 7, 1157.