Structural probing of ketone catalysts for asymmetric epoxidation

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8475-8485

  Tu, Yong ^a   Wang, Zhi Xian ^a   Frohn, Michael ^a   He, Mingqi ^a   Yu, Hongwu ^a   Tang, Yong ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; KETONE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; EPOXIDATION; STEREOCHEMISTRY;

EID: 0032514833     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9817218     Document Type: Article

References (69)

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2. For general leading references on dioxiranes see: (a) Murray, R. W. Chem. Rev. 1989, 89, 1187. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811. (d) Clennan, E. L. Trends Org. Chem. 1995, 5, 231. (e) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581.
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5. For general leading references on dioxiranes see: (a) Murray, R. W. Chem. Rev. 1989, 89, 1187. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811. (d) Clennan, E. L. Trends Org. Chem. 1995, 5, 231. (e) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581.
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8. For examples of in situ generation of dioxiranes see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758. (c) Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684.
9. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925. (f) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (h) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964. (k) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839. (l) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810.
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11. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925. (f) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (h) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964. (k) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839. (l) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810.
12. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925. (f) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (h) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964. (k) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839. (l) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810.
13. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925. (f) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (h) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964. (k) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839. (l) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810.
14. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925. (f) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (h) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964. (k) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839. (l) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810.
15. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925. (f) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (h) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964. (k) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839. (l) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810.
16. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925. (f) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (h) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964. (k) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839. (l) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810.
17. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925. (f) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (h) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964. (k) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839. (l) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810.
18. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
19. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
20. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
21. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
22. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
23. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
24. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
25. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
26. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
27. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
28. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
29. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
30. For leading references on asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Reference 2h. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Bergbreiter, D. E. Chemtracts: Organ. Chem. 1997, 10, 661. (k) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (l) Dakin, L. A.; Panek, J. S. Chemtracts: Organ. Chem. 1998, 11, 531. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
31. (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
32. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62, 2328.
33. (c) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
34. (d) Frohn, M.; Dalkiewicz, M.; Tu, Y.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 2948.
35. (e) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 3099.
36. (f) Cao, G.-A.; Wang, Z.-X.; Tu, Y.; Shi. Y. Tetrahedron Lett. 1998, 39, 4425.
37. For leading references on the discussion of the pathways see: refs 1, 2a-c,h.
38. High enantioselectivity has been obtained for the epoxidation of 4,4′-substituted stilbenes using ketones in which the chiral element is actually away from the carbonyl group (see: refs 3e,f,m).
39. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
40. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
41. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
42. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
43. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
44. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
45. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
46. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
47. For some leading references on the stability and decomposition of dioxiranes see: (a) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847. (b) Baumstark, A. L.; Beeson, M.; Vasquez, P. C. Tetrahedron Lett. 1989, 30, 5567. (c) Camporeale, M.; Fiorani, T.; Troisi, L.; Adam, W.; Curci, R.; Edwards, J. O. J. Org. Chem. 1990, 55, 93. (d) Adam, W.; Curci, R.; Gonzalez Nunez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654. (e) Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346. (f) Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263. (g) Hull, L. A.; Budhai, L. Tetrahedron Lett. 1993, 34, 5039. (h) Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981. (i) Bouchard, J.; Maine, C.; Berry, R. M.; Argyropoulos, D. S. Can. J. Chem. 1996, 74, 232.
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