New C2-symmetric chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins

Tetrahedron Asymmetry

Volumn 8, Issue 17, 1997, Pages 2921-2926

  Song, Choong Eui ^a   Kim, Yang Hee ^a   Lee, Kyo Chul ^a   Lee, Sang Gi ^a   Jin, Byung Woo ^b  

^a Korea Institute of Science and Technology   (South Korea)

^b Chong Kun Dang Research Institute   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; KETONE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHIRALITY; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030865630     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00352-2     Document Type: Article

References (21)

1. (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993 and references therein.
2. (b) Chang, S.; Lee, N. H.; Jacobsen, E. N. J. Org. Chem. 1993, 58, 6939.
3. (a) Rebek, J. Heterocycles 1981, 15, 517 and references therein.
4. (b) Davis, F. A.; Harakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123.
5. (c) Davis, F. A.; Chattopadhyay, S. Tetrahedron Lett. 1986, 27, 5079.
6. (d) Davis, F. A.; ThimmaReddy, R.; McCauley, J. P.; Przeslawski, R. M.; Harakal, M. E. J. Org. Chem. 1991, 56, 809.
7. For recent reviews on dioxirane chemisty, see: (a) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem., 1995, 67, 811.
8. (b) Curci, R. In Advances in Oxygenated Process; Baumstark, A. L., Ed.; JAI: Greenwich CT, 1990; Vol 2, Chapter I, pp 1-59.
9. (c) Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; W. Ando, Ed.; Wiley, New York, 1992, Chapter 4, pp. 195-219.
10. (a) Curci, R.; Fiorentino, M.; Serio, M. R. Chem. Commun. 1984, 155.
11. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831.
12. (c) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587.
13. (d) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491.
14. (e) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
15. Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63.
16. Armstrong, A.; Clarke, P. A.; and Wood, A. Chem. Commun. 1996, 849.
17. 2O solvent system.
18. The X-ray data of 8 will be published later.
19. Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887.
20. (a) trans-Stilbene oxide: Berti, G.; Bottari, F.; Ferrani, P. L.; Machia, B. J. Org. Chem. 1965, 30, 4091.
21. (b) trans-β-Methyl styrene oxide: Audier, H. E.; Dupin, J. F.; Tullien, J. Bull. Soc. Chim. Fr. 1996, 2811.