A C2 symmetric chiral ketone for catalytic asymmetric epoxidation of unfunctionalized olefins

Journal of the American Chemical Society

Volumn 118, Issue 2, 1996, Pages 491-492

  Yang, Dan ^a   Yip, Yiu Chung ^a   Tang, Man Wai ^a   Wong, Man Kin ^a   Zheng, Jian Hua ^a,b   Cheung, Kung Kai ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3643086474     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9529549     Document Type: Article

References (50)

1. (a) Adam, W.; Curci, R.; Edward, J. O. Acc. Chem. Res. 1989, 22, 205.
2. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187.
3. (c) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2. p 1.
4. (d) Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4.
5. (e) Adam, W.; Hadjiarapoglou, L. P. In Topics in Current Chemistry; Springer-Verlag: Berlin, 1993; Vol. 164, p 45.
6. For recent examples of dioxirane epoxidation, see: (a) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112. (b) Mello, R.; Ciminale, F.; Fiorentino, M.; Fusco, C.; Prencipe, T.; Curci, R. Tetrahedron Lett. 1990, 31, 6097. (c) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437. (d) Lluch, A.-M.; Sanchez-Baeza, F.; Messeguer, A.; Fusco, C.; Curci, R. Tetrahedron 1993, 49, 6299.
7. For recent examples of dioxirane epoxidation, see: (a) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112. (b) Mello, R.; Ciminale, F.; Fiorentino, M.; Fusco, C.; Prencipe, T.; Curci, R. Tetrahedron Lett. 1990, 31, 6097. (c) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437. (d) Lluch, A.-M.; Sanchez-Baeza, F.; Messeguer, A.; Fusco, C.; Curci, R. Tetrahedron 1993, 49, 6299.
8. For recent examples of dioxirane epoxidation, see: (a) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112. (b) Mello, R.; Ciminale, F.; Fiorentino, M.; Fusco, C.; Prencipe, T.; Curci, R. Tetrahedron Lett. 1990, 31, 6097. (c) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437. (d) Lluch, A.-M.; Sanchez-Baeza, F.; Messeguer, A.; Fusco, C.; Curci, R. Tetrahedron 1993, 49, 6299.
9. For recent examples of dioxirane epoxidation, see: (a) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112. (b) Mello, R.; Ciminale, F.; Fiorentino, M.; Fusco, C.; Prencipe, T.; Curci, R. Tetrahedron Lett. 1990, 31, 6097. (c) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437. (d) Lluch, A.-M.; Sanchez-Baeza, F.; Messeguer, A.; Fusco, C.; Curci, R. Tetrahedron 1993, 49, 6299.
10. (a) Murray, R. W.; Rajadhyaksha, S. N.; Mohan, L. J. Org. Chem. 1989, 54, 5783.
11. (b) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 1981.
12. (c) Colonna, S.; Gaggero, N. Tetrahedron Lett. 1989, 30, 6233.
13. (d) Ferrer, M.; Sanchez-Baeza, F.; Messeguer, A.; Diez, A.; Rubiralta, M. J. Chem. Soc., Chem. Commun. 1995, 293.
14. (a) Kuck, D.; Schuster, A.; Fusco, C.; Fiorentino, M.; Curci, R. J. Am. Chem. Soc. 1994, 116, 2375.
15. (b) Murray, R. W.; Jeyarman, R.; Mohan, L. J. Am. Chem. Soc. 1986, 108, 2470.
16. (c) Adam, W.; Asensio, G.; Curci, R.; Gonzalez-Nunez, M. E.; Mello, R. J. Org. Chem. 1992, 57, 953.
17. (d) Reference 2a.
18. (e) Bach, R. D.; Andres, J. L.; Su, M.-D.; McDouall, J. J. W. J. Am. Chem. Soc. 1993, 115, 5768.
19. For examples, see: (a) Dushin, R. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1992, 114, 3471. (b) Adam, W.; Hadjiarapoelou, L. P.; Jagger, V.; Klicic, J.; Seidel, B.; Wang, X. Chem. Ber. 1991, 124, 2361. (c) Adam, W.; Hadjiarapoglou, L.; Nestler, B. Tetrahedron Lett. 1990, 31, 331. (d) Adam, W.; Hadjiarapoglou, L.; Wang, X. Tetrahedron Lett. 1991, 32, 1295.
20. For examples, see: (a) Dushin, R. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1992, 114, 3471. (b) Adam, W.; Hadjiarapoelou, L. P.; Jagger, V.; Klicic, J.; Seidel, B.; Wang, X. Chem. Ber. 1991, 124, 2361. (c) Adam, W.; Hadjiarapoglou, L.; Nestler, B. Tetrahedron Lett. 1990, 31, 331. (d) Adam, W.; Hadjiarapoglou, L.; Wang, X. Tetrahedron Lett. 1991, 32, 1295.
21. For examples, see: (a) Dushin, R. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1992, 114, 3471. (b) Adam, W.; Hadjiarapoelou, L. P.; Jagger, V.; Klicic, J.; Seidel, B.; Wang, X. Chem. Ber. 1991, 124, 2361. (c) Adam, W.; Hadjiarapoglou, L.; Nestler, B. Tetrahedron Lett. 1990, 31, 331. (d) Adam, W.; Hadjiarapoglou, L.; Wang, X. Tetrahedron Lett. 1991, 32, 1295.
22. For examples, see: (a) Dushin, R. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1992, 114, 3471. (b) Adam, W.; Hadjiarapoelou, L. P.; Jagger, V.; Klicic, J.; Seidel, B.; Wang, X. Chem. Ber. 1991, 124, 2361. (c) Adam, W.; Hadjiarapoglou, L.; Nestler, B. Tetrahedron Lett. 1990, 31, 331. (d) Adam, W.; Hadjiarapoglou, L.; Wang, X. Tetrahedron Lett. 1991, 32, 1295.
23. (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758.
24. (b) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577.
25. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391.
26. (d) Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887.
27. Pioneering work by Curci et al. demonstrated that, for unfunctionalized olefins, epoxidation catalyzed by acyclic chiral ketones gave up to 20% ee. 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.
28. Pioneering work by Curci et al. demonstrated that, for unfunctionalized olefins, epoxidation catalyzed by acyclic chiral ketones gave up to 20% ee. 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.
29. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587.
30. For a recent review on catalytic asymmetric epoxidation of unfunctionalized olefins, see: Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.: VCH: New York, 1993: Chapter 4.2.
31. For recent examples on asymmetric synthesis of trans epoxides from trans olefins, see: (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. (c) Sakaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300. (d) Hosoya, N.; Hatayama, A.; Yanai, K.; Fujii, H.; Irie, R.; Katsuki, T. Synlett 1993, 641. (e) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834. (f) 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. For examples on asymmetric synthesis of trans epoxides from cis olefins using chiral Mn- salen catalysts, see: (g) Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533. (h) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
32. For recent examples on asymmetric synthesis of trans epoxides from trans olefins, see: (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. (c) Sakaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300. (d) Hosoya, N.; Hatayama, A.; Yanai, K.; Fujii, H.; Irie, R.; Katsuki, T. Synlett 1993, 641. (e) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834. (f) 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. For examples on asymmetric synthesis of trans epoxides from cis olefins using chiral Mn- salen catalysts, see: (g) Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533. (h) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
33. For recent examples on asymmetric synthesis of trans epoxides from trans olefins, see: (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. (c) Sakaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300. (d) Hosoya, N.; Hatayama, A.; Yanai, K.; Fujii, H.; Irie, R.; Katsuki, T. Synlett 1993, 641. (e) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834. (f) 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. For examples on asymmetric synthesis of trans epoxides from cis olefins using chiral Mn- salen catalysts, see: (g) Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533. (h) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
34. For recent examples on asymmetric synthesis of trans epoxides from trans olefins, see: (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. (c) Sakaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300. (d) Hosoya, N.; Hatayama, A.; Yanai, K.; Fujii, H.; Irie, R.; Katsuki, T. Synlett 1993, 641. (e) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834. (f) 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. For examples on asymmetric synthesis of trans epoxides from cis olefins using chiral Mn- salen catalysts, see: (g) Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533. (h) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
35. For recent examples on asymmetric synthesis of trans epoxides from trans olefins, see: (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. (c) Sakaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300. (d) Hosoya, N.; Hatayama, A.; Yanai, K.; Fujii, H.; Irie, R.; Katsuki, T. Synlett 1993, 641. (e) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834. (f) 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. For examples on asymmetric synthesis of trans epoxides from cis olefins using chiral Mn- salen catalysts, see: (g) Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533. (h) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
36. For recent examples on asymmetric synthesis of trans epoxides from trans olefins, see: (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. (c) Sakaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300. (d) Hosoya, N.; Hatayama, A.; Yanai, K.; Fujii, H.; Irie, R.; Katsuki, T. Synlett 1993, 641. (e) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834. (f) 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. For examples on asymmetric synthesis of trans epoxides from cis olefins using chiral Mn- salen catalysts, see: (g) Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533. (h) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
37. For recent examples on asymmetric synthesis of trans epoxides from trans olefins, see: (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. (c) Sakaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300. (d) Hosoya, N.; Hatayama, A.; Yanai, K.; Fujii, H.; Irie, R.; Katsuki, T. Synlett 1993, 641. (e) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834. (f) 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. For examples on asymmetric synthesis of trans epoxides from cis olefins using chiral Mn- salen catalysts, see: (g) Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533. (h) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
38. For recent examples on asymmetric synthesis of trans epoxides from trans olefins, see: (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. (c) Sakaki, H.; Irie, R.; Katsuki, T. Synlett 1993, 300. (d) Hosoya, N.; Hatayama, A.; Yanai, K.; Fujii, H.; Irie, R.; Katsuki, T. Synlett 1993, 641. (e) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834. (f) 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. For examples on asymmetric synthesis of trans epoxides from cis olefins using chiral Mn- salen catalysts, see: (g) Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533. (h) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
39. For highly enantioselective epoxidation of conjugated trisubstituted olefins using chiral Mn-salen catalysts, see: (a) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378. (b) Palucki, M., McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457. For asymmetric epoxidation of trisubstituted olefins catalyzed by enzymes, see: (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (d) Koch, A.; Reymond, J.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803.
40. For highly enantioselective epoxidation of conjugated trisubstituted olefins using chiral Mn-salen catalysts, see: (a) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378. (b) Palucki, M., McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457. For asymmetric epoxidation of trisubstituted olefins catalyzed by enzymes, see: (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (d) Koch, A.; Reymond, J.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803.
41. For highly enantioselective epoxidation of conjugated trisubstituted olefins using chiral Mn-salen catalysts, see: (a) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378. (b) Palucki, M., McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457. For asymmetric epoxidation of trisubstituted olefins catalyzed by enzymes, see: (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (d) Koch, A.; Reymond, J.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803.
42. For highly enantioselective epoxidation of conjugated trisubstituted olefins using chiral Mn-salen catalysts, see: (a) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378. (b) Palucki, M., McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457. For asymmetric epoxidation of trisubstituted olefins catalyzed by enzymes, see: (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (d) Koch, A.; Reymond, J.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803.
43. Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M-K.; Cheung, K.-K. Manuscript in preparation.
44. Ketone 3 was synthesized in one step from diphenic acid and 1,3-dihydroxyacerone in 45% yield using 2-chloro-1-methylpyridinium iodide as the coupling reagent (Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49).
45. 3 is needed to buffer the silica gel during column chromatography (see supporting information).
46. Chiral ketone 4 was synthesized in one step from chiral 1,1′-binaphthyl-2,2′-dicarboxylic acid and 1,3-dihydroxyacetone in 20-30% yield using 2-chloro-1-methylpyridinium iodide as the coupling reagent (see ref 13).
47. # = 0.042 (the details of the X-ray analysis are provided as supporting information).
48. Chiral ketone 4 was recovered in over 90% yield by flash column chromatography (see supporting information) and was reused without loss of chiral induction.
49. (a) Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791.
50. (b) Reference 10b.