메뉴 건너뛰기




Volumn 63, Issue 9, 1998, Pages 3099-3104

A pH Study on the Chiral Ketone Catalyzed Asymmetric Epoxidation of Hydroxyalkenes

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0001750007     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972106r     Document Type: Article
Times cited : (144)

References (44)
  • 1
    • 6044269298 scopus 로고    scopus 로고
    • For general leading references on dioxiranes, see: (a) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. Curci, R.; Dinoi, A.; Rubino M. F. Pure Appl. Chem. 1995, 67, 811-822. Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
    • (1989) Chem. Rev. , vol.89 , pp. 1187-1201
    • Murray, R.W.1
  • 2
    • 0001742543 scopus 로고
    • For general leading references on dioxiranes, see: (a) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. Curci, R.; Dinoi, A.; Rubino M. F. Pure Appl. Chem. 1995, 67, 811-822. Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
    • (1989) Acc. Chem. Res. , vol.22 , pp. 205-211
    • Adam, W.1    Curci, R.2    Edwards, J.O.3
  • 3
    • 84948351019 scopus 로고
    • For general leading references on dioxiranes, see: (a) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. Curci, R.; Dinoi, A.; Rubino M. F. Pure Appl. Chem. 1995, 67, 811-822. Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
    • (1995) Pure Appl. Chem. , vol.67 , pp. 811-822
    • Curci, R.1    Dinoi, A.2    Rubino, M.F.3
  • 4
    • 6044269298 scopus 로고    scopus 로고
    • For general leading references on dioxiranes, see: (a) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. Curci, R.; Dinoi, A.; Rubino M. F. Pure Appl. Chem. 1995, 67, 811-822. Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
    • (1996) Bull. Soc. Chim. Belg. , vol.105 , pp. 581-599
    • Adam, W.1    Smerz, A.K.2
  • 5
    • 27844577489 scopus 로고
    • For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
    • (1979) Photochem. Photobiol. , vol.30 , pp. 63-70
    • Edwards, J.O.1    Pater, R.H.2    Curci, R.3    Di Furia, F.4
  • 6
    • 24044469796 scopus 로고
    • For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
    • (1980) J. Org. Chem. , vol.45 , pp. 4758-4760
    • Curci, R.1    Fiorentino, M.2    Troisi, L.3    Edwards, J.O.4    Pater, R.H.5
  • 7
    • 33845556406 scopus 로고
    • For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
    • (1981) Org. Chem. , vol.46 , pp. 1684-1688
    • Gallopo, A.R.1    Edwards, J.O.J.2
  • 8
    • 0001131426 scopus 로고
    • For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
    • (1982) J. Org. Chem. , vol.47 , pp. 2670-2673
    • Cicala, G.1    Curci, R.2    Fiorentino, M.3    Laricchiuta, O.4
  • 9
    • 33845375878 scopus 로고
    • For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
    • (1986) J. Org. Chem. , vol.51 , pp. 1925-1926
    • Corey, P.F.1    Ward, F.E.2
  • 10
    • 33751154457 scopus 로고
    • and references therein
    • For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
    • (1995) J. Org. Chem. , vol.60 , pp. 3887-3889
    • Yang, D.1    Wong, M.K.2    Yip, Y.C.3
  • 11
    • 0000225906 scopus 로고
    • and references therein
    • For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
    • (1995) J. Org. Chem. , vol.60 , pp. 1391-1407
    • Denmark, S.E.1    Forbes, D.C.2    Hays, D.S.3    DePue, J.S.4    Wilde, R.G.5
  • 12
    • 37049107720 scopus 로고
    • 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. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) 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. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 155-156
    • Curci, R.1    Fiorentino, M.2    Serio, M.R.3
  • 13
    • 0029118915 scopus 로고
    • 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. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) 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. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5831-5834
    • Curci, R.1    D'Accolti, L.2    Fiorentino, M.3    Rosa, A.4
  • 14
    • 85034462869 scopus 로고    scopus 로고
    • See ref 2g
    • 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. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) 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. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
  • 15
    • 0028937666 scopus 로고
    • 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. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) 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. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
    • (1995) Tetrahedron , vol.51 , pp. 3587-3606
    • Brown, D.S.1    Marples, B.A.2    Smith, P.3    Walton, L.4
  • 16
    • 3643086474 scopus 로고    scopus 로고
    • 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. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) 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. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 491-492
    • Yang, D.1    Yip, Y.C.2    Tang, M.W.3    Wong, M.K.4    Zheng, J.H.5    Cheung, K.K.6
  • 17
    • 0029923940 scopus 로고    scopus 로고
    • 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. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) 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. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11311-11312
    • Yang, D.1    Wang, X.-C.2    Wong, M.-K.3    Yip, Y.-C.4    Tang, M.-W.5
  • 18
    • 0030865630 scopus 로고    scopus 로고
    • 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. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) 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. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2921-2926
    • Song, C.E.1    Kim, Y.H.2    Lee, K.C.3    Lee, S.G.4    Jin, B.W.5
  • 22
    • 0001131426 scopus 로고
    • For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
    • (1982) J. Org. Chem. , vol.47 , pp. 2670-2673
    • Cicala, G.1    Curci, R.2    Fiorentino, M.3    Laricchiuta, O.4
  • 23
    • 0028952675 scopus 로고
    • For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2437-2440
    • Murray, R.W.1    Singh, M.2    Williams, B.L.3    Moncrieff, H.M.4
  • 24
    • 0028864328 scopus 로고
    • For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
    • (1995) Tetrahedron , vol.51 , pp. 13039-13044
    • Adam, W.1    Smerz, A.K.2
  • 25
    • 0000764337 scopus 로고
    • For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
    • (1995) J. Org. Chem. , vol.61 , pp. 3506-3510
    • Adam, W.1    Smerz, A.K.2
  • 26
    • 0001451148 scopus 로고    scopus 로고
    • For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
    • (1996) J. Org. Chem. , vol.61 , pp. 1830-1841
    • Murray, R.W.1    Singh, M.2    Williams, B.L.3    Moncrieff, H.M.4
  • 27
    • 85034462665 scopus 로고    scopus 로고
    • See ref 1d
    • For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
  • 28
    • 0003727060 scopus 로고    scopus 로고
    • For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
    • (1997) Liebigs Ann./Rec. , pp. 1365-1369
    • Adam, W.1    Mitchell, C.M.2    Paredes, R.3    Smerz, A.K.4    Veloza, A.5
  • 29
    • 85034484749 scopus 로고    scopus 로고
    • It should be noted that dioxirane 2 was very short-lived. It has been extremely difficult to isolate this species. In this case, it was hoped that some dioxirane would remain within a short time
    • It should be noted that dioxirane 2 was very short-lived. It has been extremely difficult to isolate this species. In this case, it was hoped that some dioxirane would remain within a short time.
  • 30
    • 0001014759 scopus 로고    scopus 로고
    • For the leading references on the epoxidation of olefins by Oxone, see: (a) Bloch, R.; Abecassis, J.; Hassan, D. J. Org. Chem. 1985, 50, 1544-1545. (b) Zhu, W.; Ford, W. T. J. Org. Chem. 1991, 56, 7022-7026. (c) See ref 5g.
    • (1985) J. Org. Chem. , vol.50 , pp. 1544-1545
    • Bloch, R.1    Abecassis, J.2    Hassan, D.3
  • 31
    • 0001349563 scopus 로고
    • For the leading references on the epoxidation of olefins by Oxone, see: (a) Bloch, R.; Abecassis, J.; Hassan, D. J. Org. Chem. 1985, 50, 1544-1545. (b) Zhu, W.; Ford, W. T. J. Org. Chem. 1991, 56, 7022-7026. (c) See ref 5g.
    • (1991) J. Org. Chem. , vol.56 , pp. 7022-7026
    • Zhu, W.1    Ford, W.T.2
  • 32
    • 0001014759 scopus 로고    scopus 로고
    • See ref 5g
    • For the leading references on the epoxidation of olefins by Oxone, see: (a) Bloch, R.; Abecassis, J.; Hassan, D. J. Org. Chem. 1985, 50, 1544-1545. (b) Zhu, W.; Ford, W. T. J. Org. Chem. 1991, 56, 7022-7026. (c) See ref 5g.
  • 33
    • 85034464049 scopus 로고    scopus 로고
    • Such hydrogen bonding is likely to enhance the epoxidation reactivity of Oxone by dispersing the negative charge of Oxone (see ref 5g)
    • Such hydrogen bonding is likely to enhance the epoxidation reactivity of Oxone by dispersing the negative charge of Oxone (see ref 5g).
  • 34
    • 0003544583 scopus 로고
    • Ojima, I., Ed.; VCH: New York, Chapter 4.1
    • For highly enantioselective epoxidation of allylic alcohols, see: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (b) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299.
    • (1993) Catalytic Asymmetric Synthesis
    • Johnson, R.A.1    Sharpless, K.B.2
  • 35
    • 0001780886 scopus 로고    scopus 로고
    • For highly enantioselective epoxidation of allylic alcohols, see: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (b) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299.
    • (1996) Org. React. , vol.48 , pp. 1-299
    • Katsuki, T.1    Martin, V.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.