Oxygen transfer reactions from an oxaziridinium tetrafluoroborate salt to olefins

Tetrahedron

Volumn 53, Issue 40, 1997, Pages 13727-13738

  Lusinchi, Xavier ^a   Hanquet, Gilles ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE;

ARTICLE; DRUG SYNTHESIS; EPOXIDATION; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030886543     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00890-9     Document Type: Article

References (52)

1. Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res., 1989, 22, 205-215.
2. Davies, F.A.; Sheppard, A.C. Tetrahedron Rep., 1989, 45, 5703-5742.
3. Jennings, W.B.; Trochanewycz, M.; Boyd, D.R. J. Chem. Soc. Chem. Commun., 1994, 2549-2551.
4. a) Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron Lett., 1988, 29, 3941-3944.
5. b) Bohé, L.; Hanquet, G.; Lusinchi, X., Milliet, P. Tetrahedron Lett., 1993, 35, 7271-7274.
6. Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron, 1993, 49, 423-438.
7. Hanquet, G.; Lusinchi, X.; Milliet, P. C.R.Acad.Sci.Paris 1991, 313 S II, 625-630.
8. a) Lynch, B.M.; Pausacker, K.H. J. Chem. Soc. 1955, Vol. II, 1525-1531.
9. b) Campbell, D.R.; Edwards, J.O.; Mac Lachlan, J.; Polgar, K. J. Am. Chem. Soc., 1958, 80, 5308-5312.
10. a) Bissing, D.E.; Speziale, A.J. J. Am. Chem. Soc., 1965, 87, 2683-2690.
11. b) Curtin, D.Y.; Kellom, D.B. J. Am. Chem. Soc., 1953, 73, 6011-6017.
12. Gerkin, R.M.; Rickborn, B. J. Am. Chem. Soc., 1967, 89, 5850-5855.
13. Boesecken, J.; Hanegraaff, J. Recl. Trav. Chim. Pays-Bas, 1942, 61, 69-75.
14. Filler, R.; Camara, B.R.; Naqvi, S.M. J. Am. Chem. Soc., 1959, 81, 658-661.
15. a) Stille, J.K.; Witherell, D.R. J. Am. Chem. Soc., 1964, 86, 2188-2192.
16. b) Kwart, H.; Takeshita, T. J. Org. Chem. 1963, 28, 670-674.
17. Greene, F.D.; Adam, W. J. Org. Chem., 1964, 29, 136-139.
18. Price, C.C.; Carmelite, D.D. J. Am. Chem. Soc., 1966, 88, 4039-4044.
19. Baret, P.; Pierre, J.L.; Heilmann, R. Bull. Soc. Chim. France, 1967, 4, 4735-4739.
20. Handley, J.R.; Swigar, A.A.; Silverstein, R.M. J. Org. Chem., 1979, 44, 2954-2955.
21. Meinwald, J.; Cadoff, B.C. J. Org. Chem., 1962, 27, 1539-1541.
22. Greene, E.A.; LeDrian, C.; Crabbé, P J. Am. Chem. Soc., 1980, 102, 7583-7584.
23. Marples, B.H.; Muxworthy, J.P.; Baggaley, K.H. Tetrahedron Lett. 1991, 32, 533-536.
24. a) Berti, G. Topics in Stereochemistry, 1973, 7, 93-217.
25. b) Barton, D.H.R. in Comprehensive Organic chemistry, 1979, 1, 861 and references herein.
26. a) Henbest, H.B.; Wilson, R.A.L. J. Chem. Soc., 1957, 1958-1965.
27. b) Kocovsky, P. Tetrahedron Lett. 1988, 29, 2475-2478.
28. a) Adam, W.; Smerz, A.K. J. Org. Chem., 1996, 61, 3506-3510.
29. b) Adam, W.; Smerz, A.K. Tetrahedron, 1995, 51, 13039-13044.
30. c) Murray, R.W.; Singh, M.; Williams, B.L.; Moncrieff, H.M. Tetrahedron Lett., 1995, 36, 2437-2440.
31. a) Adam, W.; Hadjiarapoglou, L.; Smerz, A.K. Chem. Ber. 1991, 1, 227-232.
32. b) Bovicelli, P; Lupattelli, P.; Mincione, E. J. Org. Chem. 1994, 15, 4304-4307.
33. c) Hanquet, G.; Lusinchi, X.; Tetrahedron, 1994, 50, 12185-12199.
34. Taildomirov, D.A.; Parafilova, O.S.; Eremeer, A.V. Khim. Geteroytikel. Soedin., 1991, 3, 406-409.
35. a) Kurihara, M.; Ito, S.; Tsusumi, N.; Miyata, N. Tetrahedron Lett., 1994, 35, 1577-1580.
36. b) Adam, W.; Prechtl, F.; Richter, F.P.; Smerz, A.K. Tetrahedron Lett., 1993, 34, 8427-8430.
37. Dess, D.B.; Martin, J.C. J. Org. Chem. 1983, 48, 4155-4156.
38. Anastassiou, A.G. J. Org. Chem. 1966, 31, 1131-1134.
39. Oberhauser, Th.; Bodentach, M.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1987, 43, 3931-3944.
40. a) Yadav, J.S.; Patil, D.G.; Krishna, R.R.; Chawla, H.O.S. Tetrahedron 1982, 38, 1003-1011.
41. b) Ranganathan, S.; Ranganathan, D.; Mehrotra, A.K. Tetrahedron Lett. 1975, 1215-1218.
42. a) Baltes, H.; Stork, L.; Schäfer, H.J. Chem. Ber. 1979, 112, 807-817.
43. b) Suhara, Y.; Minami, J. Bull. Chem. Soc. Jpn. 1966, 39, 1968-1971.
44. Yadav, J.S.; Deshpande, P.K.; Sharma, G.V.M. Tetrahedron 1990, 46, 7033-7046.
45. Mihailovic, M.L.; Pavloric, N.: Gojlevic, S. Glas. Hem. Drus. Beograd. 1975, 40, 309-315.
46. a) Cross, A.D. J. Am. Chem. Soc. 1962, 84, 3206-3208.
47. b) Fieser, L.F.; Fieser, M.in«Reagents for Organic Synthesis» 1967, Vol I, 136.
48. a) Jankowski, K., Daigle, J. Y. Can. J. Chem. 1971, 49, 2594-2597.
49. b) Mori, K.; Hazra, B.G.; Pfeiffer, R.J.; Gupla, A.K.; Lindgren, B.S. Tetrahedron 1987, 43, 2249-2254.
50. c) Kaneda, K.; Itoh, T.; Fujiwara, Y.; Teranishi, S. Bull. Chem. soc. Jpn 1973, 46, 3810-3814.
51. Dalton, D.R.; Putta, D.P.; Jones, D.C. J. Am. Chem. Soc. 1968, 90, 5498-5501.
52. Sainsbury, M.; Pyka, S.F.; Brown, D.; Lugton, W.G.D. Tetrahedron 1968, 24, 427-439.