Asymmetric C-H oxidation of vic-diols to α-hydroxy ketones by a fructose-derived dioxirane: Electronic effects on the enantioselectivity of oxygen transfer

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7492-7497

  Adam, Waldemar ^a   Saha Möller, Chantu R ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ETHYLENE OXIDE; FRUCTOSE; HYDROGEN; KETONE; OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ENANTIOMER; HYDROGEN BOND; OPTICAL ROTATION; OXIDATION; STEREOCHEMISTRY;

EID: 0345466517     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9907843     Document Type: Article

References (66)

1. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853.
2. (b) Adam, W.; Bialas, J.; Hadjiarapoglou, L. P. Chem. Ber. 1991, 124, 2377.
3. Curci, R.; Fiorentino, M.; Triosi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760.
4. (b) Adam, W.; Hadjiarapogolou, L. P.; Smerz, A. Chem. Ber. 1991, 124, 227-232.
5. (c) Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889.
6. (d) Denmark, S. E.; Wu, Z. J. Org. Chem. 1997, 62, 8964-8965.
7. (e) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810-2811.
8. (f) Frohn, M.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 6425-6426.
9. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
10. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201.
11. (c) Curci, R. In Advances in Oxygenated Process; Baumstark, A. L., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, Chapter I, pp 1-59.
12. (d) Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 4, pp 195-219.
13. (e) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822.
14. (f) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1998, 105, 581-599.
15. (g) Adam, W.; Smerz, A. K.; Zhao, C.-G. J. Prakt. Chem. 1997, 339, 298-300.
16. Murray, R. W.; Jeyaraman, R.; Mohan, L. J. Am. Chem. Soc. 1986, 108, 2470-2472.
17. (b) Mello, R.; Fiorentino, M.; Fusco, C.; Curci, R. J. Am. Chem. Soc. 1989, 111, 6749-6757.
18. Bravo, A.; Fontana, F.; Fronza, G.; Minisci, F.; Zhao, L. J. Org. Chem. 1998, 63, 254-263.
19. (b) Vanni, R.; Garden, S. J.; Banks, J. T.; Ingold, K. U. Tetrahedron Lett. 1995, 36, 7999-8002.
20. Adam, W.; Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Gasparrini, F.; Kluge, R.; Paredes, R.; Schulz, M.; Smerz, A. K.; Veloza, L. A.; Weinkötz, S.; Winde, R. Chem. Eur. J. 1997, 3, 105-109.
21. (b) Simakov, P. A.; Choi, S.-Y.; Newcomb, M. Tetrahedron Lett. 1998, 39, 8187-8190.
22. Shustov, G. V.; Rauk, A. J. Org. Chem. 1998, 63, 5413-5422.
23. (b) Du, X.; Houk, K. N. J. Org. Chem. 1998, 63, 6480-6483.
24. (c) Glukhovtsev, M. N.; Canepa, C.; Bach, R. D. J. Am. Chem. Soc. 1998, 120, 10528-10533.
25. Punniyamurthy, T.; Miyafuji, A.; Katsuki, T. Tetrahedron Lett. 1998, 39, 8295-8298.
26. (b) Miyafuji, A.; Katsuki, T. Tetrahedron 1998, 54, 10339-10348.
27. (c) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337-6350.
28. (d) Södergen, M. J.; Andersson, P. G. Tetrahedron Lett. 1996, 37, 7577-7580.
29. (e) Hamada, T.; Irie, R.; Mihara, J.; Hamachi, K.; Katsuki, T. Tetrahedron 1998, 54, 10017-10028.
30. (f) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628-3634.
31. Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
32. (b) Arndsten, B. A.; Bergman, R. G.; Mobley, A.; Peterson, P. H. Acc. Chem. Res. 1992, 25, 504-512.
33. (c) Asensio, G.; González-Núñez, M. E.; Bernardini, C. B.; Mello, R.; Adam, W. J. Am. Chem. Soc. 1993, 115, 7250-7253.
34. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69-72.
35. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach, Pergamon: New York, 1983; Chapter 2.
36. (b) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919-934.
37. Adam, W.; Fell, R. T.; Saha-Möller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397-401.
38. (b) Zhu, Y.; Tu, Y.; Yu, H.; Shi, Y. Tetrahedron Lett. 1998, 39, 7819-7822.
39. Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806-9807.
40. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62, 2328-2329.
41. (c) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224-11235.
42. Curci, R.; D'Accolti, L.; Detomaso, A.; Fusco, C.; Takeuchi, K.; Ohga, Y.; Eaton, P.; Yip, Y.-C. Tetrahedron Lett. 1993, 34, 4559-4562.
43. (b) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600-3601.
44. (c) Bovicelli, P.; Lupattelli, P.; Sanetti, A.; Mincione, E. Tetrahedron Lett. 1995, 36, 3031-3034.
45. (d) Bovicelli, P.; Sanetti, A.; Lupattelli, P. Tetrahedron 1996, 52, 10969-10978.
46. 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.
47. (b) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
48. (c) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622-8623.
49. (d) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995-3998.
50. (e) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S.-g.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
51. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi. H. J. Org. Chem. 1997, 62, 8288-8289.
52. (g) 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, 720, 5943-5952.
53. (h) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659-7660.
54. (i) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621-622.
55. (j) Tu, Y.; Wang, Z.-X.; Frohn, M.; He, M.; Yu, H.; Tang, Y.; Shi, Y. J. Org. Chem. 1998, 63, 8475-8485.
56. Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 4117-4122.
57. Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221.
58. (b) Gu, J. X.; Li, Z. Y.; Lin, G. Q. Chin. Chem. Lett. 1995, 6, 457-458.
59. Adam, W.; Díaz, M. T.; Fell, R. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1996, 7, 2207-2210.
60. (b) Davis, F. A.; Shepperd, A. C.; Chen, B.-C.; Hague, M. S. J. Am. Chem. Soc. 1990, 112, 6679-6690.
61. The oxidation of 1-phenyl-1,2-propanediol by dimethyldioxirane (DMD) gave a mixture of 2-hydroxy-1-phenyl-1-propanone, 1-hydroxy-1-phenyl-2-propanone, and 1-phenyl-1,2-propanedione in a ratio of 52: 32:16 (see ref 13d).
62. Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Rosa, A. Tetrahedron Lett. 1996, 37, 115-118.
63. DMD oxidizes acetal-4c regioselectively to give the 2-hydroxy-1-phenyl-1-propanone as the only product (see refs 13c and 19).
64. Exner, O.; In Correlation Analysis in Chemistry; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1978; Chapter 10.
65. (b) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
66. Steric factors should not be responsible for the low reactivity of the acetals toward the fructose-derived dioxirane since these substrates are also much less reactive towards dimethyldioxirane (DMD) than the corresponding diols (see ref 19).