A Dramatic pH Effect Leads to a Catalytic Asymmetric Epoxidation

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2328-2329

  Wang, Zhi Xian ^a   Tu, Yong ^a   Frohn, Michael ^a   Shi, Yian ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001554971     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962392r     Document Type: Article

References (39)

1. For leading references on asymmetric epoxidations see: (a) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (d) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (e) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927. (f) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742 and references cited therein. (g) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392.
2. For leading references on asymmetric epoxidations see: (a) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (d) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (e) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927. (f) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742 and references cited therein. (g) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392.
3. For leading references on asymmetric epoxidations see: (a) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (d) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (e) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927. (f) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742 and references cited therein. (g) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392.
4. For leading references on asymmetric epoxidations see: (a) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (d) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (e) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927. (f) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742 and references cited therein. (g) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392.
5. For leading references on asymmetric epoxidations see: (a) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (d) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (e) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927. (f) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742 and references cited therein. (g) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392.
6. For leading references on asymmetric epoxidations see: (a) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (d) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (e) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927. (f) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742 and references cited therein. (g) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392.
7. For leading references on asymmetric epoxidations see: (a) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (d) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (e) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927. (f) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742 and references cited therein. (g) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392.
8. For general reviews on dioxiranes see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822.
9. For general reviews on dioxiranes see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822.
10. For general reviews on dioxiranes see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822.
11. For examples of in situ generation of dioxiranes see: (a) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (b) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
12. For examples of in situ generation of dioxiranes see: (a) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (b) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
13. For examples of in situ generation of dioxiranes see: (a) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (b) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
14. For examples of asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (d) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (e) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
15. For examples of asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (d) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (e) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
16. For examples of asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (d) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (e) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
17. For examples of asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (d) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (e) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
18. For examples of asymmetric epoxidation mediated by chiral ketones see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (d) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (e) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
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25. 2, MeOH. and water as solvents: Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577-1580.
26. (a) There is a report showing that the catalytic efficiency of cyclohexanone for the oxidation of pyridine with Oxone is maximized at a slightly higher pH (8.5). The data suggest that at this pH the Baeyer-Villiger process of cyclohexanone is minimized; see: Gallopo, A. R.; Edwards, J. O. J. Org. Chem. 1981, 46, 1684-1688. (b) There is also a report suggesting that the Baeyer-Villiger reaction might become significant at high pH values (pH > 11); see ref 6a.
27. (a) There is a report showing that the catalytic efficiency of cyclohexanone for the oxidation of pyridine with Oxone is maximized at a slightly higher pH (8.5). The data suggest that at this pH the Baeyer-Villiger process of cyclohexanone is minimized; see: Gallopo, A. R.; Edwards, J. O. J. Org. Chem. 1981, 46, 1684-1688. (b) There is also a report suggesting that the Baeyer-Villiger reaction might become significant at high pH values (pH > 11); see ref 6a.
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33. Under these conditions the epoxidation in the absence of the ketone catalyst is negligible within 1.5 h reaction time.
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