Probing for steric and electronic effects in diastereoselective dioxirane epoxidations compared to the oxygen transfer by peroxy acids

Liebigs Annales

Volumn , Issue 3, 1997, Pages 547-551

  Adam, Waldemar ^a   Paredes, Rodrigo ^b   Smerz, Alexander K ^a   Veloza, L Angela ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSIDAD DEL VALLE   (Colombia)

Author keywords

Diastereoselectivity; Dioxiranes; Epoxidations; Peracids; Spiro transition states

Indexed keywords

EID: 33748824782     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970316     Document Type: Review

References (64)

1. [1a] R. W. Murray, R. J. Jeyaraman, J. Org. Chem. 1985, 50, 2847-2853.
2. [1b] W. Adam, L. Hadjiarapoglou, J. Bialas, Chem. Ber. 1991, 124, 2377.
3. [2a] W. Adam, R. Curci, J. O. Edwards, Acc. Chem. Res. 1989, 22, 205-211.
4. [2b] R. W. Murray, Chem. Rev. 1989, 89, 1187-1201.
5. [2c] R. Curci, in Advances in Oxygenated Processes (Ed.: A. L. Baumstark), JAI, Greenwich, CT, 1990, Vol. 2, Chapter I, pp. 1-55.
6. [2d] W. Adam, L. P. Hadjiarapoglou, R. Curci, R. Mello, in Organic Peroxides (Ed.: W. Ando), Wiley, New York, 1992, Chapter 4, pp 195-219.
7. [2e] W. Adam, L. Hadjiarapoglou, Top. Curr. Chem. 1993, 164, 45-62.
8. [2f] R. Curci, A. Dinoi, M. F. Rubino, Pure Appl. Chem. 1995, 67, 811-822.
9. [2g] W. Adam, A. K. Smerz, Bull. Soc. Chim. Belg. 1996, 105, 581-599.
10. [3a] W. Adam, L. Hadjiarapoglou, K. Peters, M. Sauter, J. Am. Chem. Soc. 1993, 115, 8603-8608.
11. [3b] W. Adam, M. Ahrweiler, K. Paulini, H.-U. Reißig, V. Voerckel, Chem. Ber. 1992, 125, 2719-2721.
12. [4a] A. L. Baumstark, P. C. Vasquez, J. Org. Chem. 1988, 53, 3437-3439.
13. [4b] R. W. Murray, D. L. Shiang, J. Chem. Soc., Perkin Trans. 2 1990, 349-352.
14. [4c] A. L. Baumstark, D. B. Harden, Jr., J. Org. Chem. 1990, 58, 7615-7618.
15. [5a] R. W. Murray, D. L. Shiang, M. Singh, J. Org. Chem. 1991, 56, 3677-3682.
16. [5b] Y. Angelis, X. Zhang, M. Orfanopoulos, Tetrahedron Lett. 1996, 37, 5991-5994.
17. A. L. Baumstark, C. J. McCloskey, Tetrahedron Lett. 1987, 28, 3311-3314.
18. G. Bouillon, C. Lick, K. Schank, in The Chemistry of Peroxides (Ed.: S. Patai), John Wiley, New York, 1983, p. 279.
19. [8a] P. D. Bartlett, Rec. Chem. Prog. 1950, 11, 47-51.
20. [8b] R. P. Hanzlik, G. O. Shearer, J. Am. Chem. Soc. 1975, 5231-5233.
21. [9a] R. D. Bach, G. J. Wolber, J. Am. Chem. Soc. 1984, 106, 1410-1415.
22. [9b] R. D. Bach, A. L. Owensby, C. Gonzales, H. B. Schlegel, J. Am. Chem. Soc. 1991, 113, 2338-2339.
23. S. Yamabe, C. Kondou, T. Minato, J. Org. Chem. 1996, 61, 616-620.
24. W. Adam, H. G. Brünker, A. S. Kumar, E.-M. Peters, K. Peters, U. Schneider, H. G. von Schnering, J. Am. Chem. Soc. 1996, 118, 1899-1905.
25. [12a] R. W. Murray, M. Singh, B. L. Williams, H. Moncrieff, Tetrahedron Lett. 1995, 36, 2437-2440.
26. [2b] W. Adam, A. K. Smerz, Tetrahedron 1995, 51, 13039-13044.
27. [12c] W. Adam, A. K. Smerz, J. Org. Chem. 1996, 61, 3506-3510.
28. M. Kurihara, S. Ito, N. Tsutsumi, N. Miyata, Tetrahedron Lett. 1994, 35, 1577-1580.
29. B. A. Marples, J. P. Muxworthy, K. H. Baggaley, Tetrahedron Lett. 1991, 32, 533-536.
30. R. W. Murray, M. Singh, R. Jeyaraman, J. Am. Chem. Soc. 1992, 114, 1346-1352.
31. [16a] R. Bloch, J. Abecassis, D. Hassan, J. Org. Chem. 1985, 50, 1544-1545.
32. [16b] W. Zhu, W. T. Ford, J. Org. Chem. 1991, 50, 7022-7026.
33. [13] ) and isolated dioxiranes (in our present study) is difficult to rationalize, especially because significantly higher d.r. values have been described for the in situ system. Moreover, our in situ control experiments (Table 1, entries 10 and 11) also reveal results that are significantly different from those reported.
34. A. Bravo, F. Fontana, G. Fronza, F. Minisci, A. Serri, Tetrahedron Lett. 1995, 36, 6945-6948.
35. [19a] H.-B. Burgi, J. D. Dunitz, Acc. Chem. Res. 1983, 16, 153-161.
36. [19b] W. Damm, B. Giese, J. Hartung, T. Hasskerl, K. N. Houk, O. Hüter, H. Zipse, J. Am. Chem. Soc. 1992, 114, 4067-4079.
37. [19c] M. W. Wong, A. Pross, L. Radom, J. Am. Chem. Soc. 1994, 116, 11938-11943.
38. G. Berti, in Topics in Stereochemistry (Eds.: N. A. Allinger, E. L. Eliel) John Wiley and Sons, New York, 1978, p. 129.
39. R. Wylde, J.-M. Teulon, Bull. Soc. Chim. Fr. 1970, 758-764.
40. B. A. McKittrick, B. Ganem, Tetrahedron Lett. 1985, 26, 4895-4898.
41. A. S. Rao, S. K. Paknikar, J. G. Kirtane, Tetrahedron 1983, 39, 2323-2367.
42. J. P. Teresa, C. Torres, M. S. Gozales, I. Sanchez Bellido, Anal. Quim. 1983, 79, 442-445.
43. While our work described herein was in progress, diastereoselective epoxidations with DMD were reported by R. W. Murray, M. Singh, B. L. Williams, H. M. Moncrieff, J. Org. Chem. 1996, 61, 1830-1841, which are in good accordance with our data.
44. E. Vedejs, W. H. Dent, III, J. T. Kendall, P. A. Oliver, J. Am. Chem. Soc. 1996, 118, 3556-3567.
45. G. D. Maynard, L. A. Paquette, J. Org. Chem. 1991, 56, 5480-5482.
46. J. Rebek, Jr., L. Marshall, J. McManis, R. Wolak, J. Org. Chem. 1986, 51, 1649-1653.
47. M. Schulz, R. Kluge, S. Liebsch, J. Lessig, M. Halik, F. Gadissa, Tetrahedron 1996, 52, 13151-13166.
48. [30a] R. Mello, F. Ciminale, M. Fiorentino, C. Fucsco, T. Prencipe, R. Curci, Tetrahedron Lett. 1990, 31, 6097-6100.
49. [30b] P. Bovicelli, P. Lupatelli, E, Mincione, T. Prencipe, R. Curci, J. Org. Chem. 1992, 57, 5052-5054.
50. [30c] W. Ebenezer, G. Pattenden, Tetrahedron Lett. 1992, 33, 4053-4056.
51. [30d] P. Bovicelli, P. Lupatelli, E. Mincione, J. Org. Chem. 1994, 59, 4304-4307.
52. W. Adam, R. Curci, L. D'Accolti, A. Dinoi, C. Fusco, F. Gasparrini, R. Kluge, R. Paredes, M. Schulz, A. K. Smerz, L. A. Veloza, S. Weinkötz, R. Winde, Chem. Eur. J. 1997, 3, 99-103.
53. [32a] D. Yang, M.-K. Wong, M.-W. Tang, Y.-C. Yip, K.-K. Cheung, 212th American Chemical Society Nat. Meeting, Orlando, FL, 1996, Poster 225.
54. [32b] Y. Tu, Z.-X. Wang, Y. Shi, J. Am. Chem. Soc. 1996, 118, 9806-9807.
55. S. Hünig, G. Märkel, J. Sauer, Integriertes Organisches Praktikum, Verlag Chemie, 1979, Weinheim, p. 134.
56. S. Siegel, M. Dunkel, G. V. Smith, W. Halpern, J. Cozart, J. Org. Chem. 1966, 31, 2802-2806.
57. B. A. McKittrick, B. Ganem, Tetrahedron Lett. 1985, 26, 4895-4898.
58. J.-Y. Koo, G. B. Schuster, J. Org. Chem. 1979, 44, 847-851.
59. G. O. Schenk, K. G. Kinkel, H. J. Mertens, Liebigs Ann. Chem. 1953, 125-156.
60. V. P. Rajan, S. N. Banore, H. N. Subbarao, S. K. Dev, Tetrahedron 1984, 40, 983-990.
61. P. Battoni, J. P. Reaud, J. F. Bartol, M. Reina-Artiles, M. Fort, D. Mansuy, J. Am. Chem. Soc. 1988, 110, 8462-8470.
62. K. L. Reed, J. T. Gupton, T. L. Solarz, Synth. Comm. 1989, 35, 3579-3587.
63. H. Heaney, Aldrichim. Acta, 1993, 26, 35-45.
64. P. Chamberlain, M. L. Roberts, G. H. Whitham, J. Chem. Soc. (B) 1970, 1374-1381.