메뉴 건너뛰기




Volumn 64, Issue 20, 1999, Pages 7675-7677

Chiral ketone-catalyzed asymmetric epoxidation of 2,2-disubstituted vinylsilanes

Author keywords

[No Author keywords available]

Indexed keywords

2 [(TERT BUTYLDIMETHYLSILOXY)METHYL] 1 (TRIMETHYLSILYL) 1 BUTENE OXIDE; 2 BENZYL 1 (TRIMETHYLSILYL) 1 HEXENE OXIDE; 2 ETHYL 1 (TRIMETHYLSILYL) 1 HEXENE OXIDE; 2 PHENYL 1 (TRIMETHYLSILYL) 1 BUTENE OXIDE; 2 PHENYL 1 (TRIMETHYLSILYL) 1 PROPENE OXIDE; 4 (TERT BUTYLDIPHENYLSILOXY) 2 ETHYL 1 (TRIMETHYLSILYL) 1 BUTENE OXIDE; 4 ETHYL 5 (TRIMETHYLSILYL) 4 PENTEN 1 OL OXIDE; 5 ETHYL 6 (TRIMETHYLSILYL) 5 HEXEN 1 OL OXIDE; KETONE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLSILANE DERIVATIVE;

EID: 0033215353     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990951z     Document Type: Article
Times cited : (99)

References (40)
  • 2
    • 33847799454 scopus 로고
    • For leading references on oxiranyl anions, see: (a) Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1876, 98, 4646. (b) Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042. (c) Mani, N. S.; Townsend, C. A. J. Org. Chem. 1997, 62, 636.
    • (1876) J. Am. Chem. Soc. , vol.98 , pp. 4646
    • Eisch, J.J.1    Galle, J.E.2
  • 3
    • 0000430715 scopus 로고
    • For leading references on oxiranyl anions, see: (a) Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1876, 98, 4646. (b) Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042. (c) Mani, N. S.; Townsend, C. A. J. Org. Chem. 1997, 62, 636.
    • (1989) J. Org. Chem. , vol.54 , pp. 4042
    • Molander, G.A.1    Mautner, K.2
  • 4
    • 0031027534 scopus 로고    scopus 로고
    • For leading references on oxiranyl anions, see: (a) Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1876, 98, 4646. (b) Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042. (c) Mani, N. S.; Townsend, C. A. J. Org. Chem. 1997, 62, 636.
    • (1997) J. Org. Chem. , vol.62 , pp. 636
    • Mani, N.S.1    Townsend, C.A.2
  • 5
    • 0000922004 scopus 로고
    • For leading references on removing the silyl group from α,β-epoxysilanes, see: (a) Chan, T. H.; Lau, P. W. K.; Li, M. P. Tetrahedron Lett. 1976, 2667. (b) Kasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 21, 4229. (c) Tomioka, H.; Suzuki, T.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3387. (d) Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280.
    • (1976) Tetrahedron Lett. , pp. 2667
    • Chan, T.H.1    Lau, P.W.K.2    Li, M.P.3
  • 6
    • 0000318510 scopus 로고
    • For leading references on removing the silyl group from α,β- epoxysilanes, see: (a) Chan, T. H.; Lau, P. W. K.; Li, M. P. Tetrahedron Lett. 1976, 2667. (b) Kasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 21, 4229. (c) Tomioka, H.; Suzuki, T.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3387. (d) Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 4229
    • Kasan, I.1    Kishi, Y.2
  • 7
    • 0001367388 scopus 로고
    • For leading references on removing the silyl group from α,β- epoxysilanes, see: (a) Chan, T. H.; Lau, P. W. K.; Li, M. P. Tetrahedron Lett. 1976, 2667. (b) Kasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 21, 4229. (c) Tomioka, H.; Suzuki, T.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3387. (d) Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 3387
    • Tomioka, H.1    Suzuki, T.2    Oshima, K.3    Nozaki, H.4
  • 8
    • 37049068900 scopus 로고
    • For leading references on removing the silyl group from α,β- epoxysilanes, see: (a) Chan, T. H.; Lau, P. W. K.; Li, M. P. Tetrahedron Lett. 1976, 2667. (b) Kasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 21, 4229. (c) Tomioka, H.; Suzuki, T.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3387. (d) Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280.
    • (1988) J. Chem. Soc., Chem. Commun. , pp. 1280
    • Chan, T.H.1    Chen, L.M.2    Wang, D.3
  • 26
    • 0001498715 scopus 로고
    • For leading references on asymmetric synthesis of terminal epoxides, see: (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 709, 5765. (b) Reference 3d. (c) Dexter, A. F.; Lakner, F. J.; Campbell, R. A.; Hager, L. P. J. Am. Chem. Soc. 1995, 117, 6412. (d) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420. (e) Tokunaga, M.; Larrow, J. F.; Kakiuchi, P.; Jacobsen, E. N. Science 1997, 277, 936. (f) Lebel, H.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 9624. (g) Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
    • (1987) J. Am. Chem. Soc. , vol.709 , pp. 5765
    • Gao, Y.1    Hanson, R.M.2    Klunder, J.M.3    Ko, S.Y.4    Masamune, H.5    Sharpless, K.B.6
  • 27
    • 0344337956 scopus 로고    scopus 로고
    • Reference 3d
    • For leading references on asymmetric synthesis of terminal epoxides, see: (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 709, 5765. (b) Reference 3d. (c) Dexter, A. F.; Lakner, F. J.; Campbell, R. A.; Hager, L. P. J. Am. Chem. Soc. 1995, 117, 6412. (d) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420. (e) Tokunaga, M.; Larrow, J. F.; Kakiuchi, P.; Jacobsen, E. N. Science 1997, 277, 936. (f) Lebel, H.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 9624. (g) Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
  • 28
    • 0000890788 scopus 로고
    • For leading references on asymmetric synthesis of terminal epoxides, see: (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 709, 5765. (b) Reference 3d. (c) Dexter, A. F.; Lakner, F. J.; Campbell, R. A.; Hager, L. P. J. Am. Chem. Soc. 1995, 117, 6412. (d) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420. (e) Tokunaga, M.; Larrow, J. F.; Kakiuchi, P.; Jacobsen, E. N. Science 1997, 277, 936. (f) Lebel, H.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 9624. (g) Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6412
    • Dexter, A.F.1    Lakner, F.J.2    Campbell, R.A.3    Hager, L.P.4
  • 29
    • 0029757771 scopus 로고    scopus 로고
    • For leading references on asymmetric synthesis of terminal epoxides, see: (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 709, 5765. (b) Reference 3d. (c) Dexter, A. F.; Lakner, F. J.; Campbell, R. A.; Hager, L. P. J. Am. Chem. Soc. 1995, 117, 6412. (d) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420. (e) Tokunaga, M.; Larrow, J. F.; Kakiuchi, P.; Jacobsen, E. N. Science 1997, 277, 936. (f) Lebel, H.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 9624. (g) Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7420
    • Larrow, J.F.1    Schaus, S.E.2    Jacobsen, E.N.3
  • 30
    • 0030860279 scopus 로고    scopus 로고
    • For leading references on asymmetric synthesis of terminal epoxides, see: (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 709, 5765. (b) Reference 3d. (c) Dexter, A. F.; Lakner, F. J.; Campbell, R. A.; Hager, L. P. J. Am. Chem. Soc. 1995, 117, 6412. (d) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420. (e) Tokunaga, M.; Larrow, J. F.; Kakiuchi, P.; Jacobsen, E. N. Science 1997, 277, 936. (f) Lebel, H.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 9624. (g) Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
    • (1997) Science , vol.277 , pp. 936
    • Tokunaga, M.1    Larrow, J.F.2    Kakiuchi, P.3    Jacobsen, E.N.4
  • 31
    • 0032567320 scopus 로고    scopus 로고
    • For leading references on asymmetric synthesis of terminal epoxides, see: (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 709, 5765. (b) Reference 3d. (c) Dexter, A. F.; Lakner, F. J.; Campbell, R. A.; Hager, L. P. J. Am. Chem. Soc. 1995, 117, 6412. (d) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420. (e) Tokunaga, M.; Larrow, J. F.; Kakiuchi, P.; Jacobsen, E. N. Science 1997, 277, 936. (f) Lebel, H.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 9624. (g) Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
    • (1998) J. Org. Chem. , vol.63 , pp. 9624
    • Lebel, H.1    Jacobsen, E.N.2
  • 32
    • 0033585578 scopus 로고    scopus 로고
    • For leading references on asymmetric synthesis of terminal epoxides, see: (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 709, 5765. (b) Reference 3d. (c) Dexter, A. F.; Lakner, F. J.; Campbell, R. A.; Hager, L. P. J. Am. Chem. Soc. 1995, 117, 6412. (d) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420. (e) Tokunaga, M.; Larrow, J. F.; Kakiuchi, P.; Jacobsen, E. N. Science 1997, 277, 936. (f) Lebel, H.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 9624. (g) Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 460
    • Collman, J.P.1    Wang, Z.2    Straumanis, A.3    Quelquejeu, M.4    Rose, E.5
  • 33
    • 0000500836 scopus 로고
    • For leading references on the transition states of the dioxirane-mediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. R. Liu, J.; DeMello, N. C., Condroski, K R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3311
    • Baumstark, A.L.1    McCloskey, C.J.2
  • 34
    • 33845280766 scopus 로고
    • For leading references on the transition states of the dioxirane- mediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. R. Liu, J.; DeMello, N. C., Condroski, K R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.
    • (1988) J. Org. Chem. , vol.53 , pp. 3437
    • Baumstark, A.L.1    Vasquez, P.C.2
  • 35
    • 0001564432 scopus 로고
    • A. L.
    • For leading references on the transition states of the dioxirane- mediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. R. Liu, J.; DeMello, N. C., Condroski, K R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7207
    • Bach, R.D.1    Andres, J.L.2    Schlegel, H.B.3    McDouall, J.J.W.4
  • 36
    • 0029923940 scopus 로고    scopus 로고
    • For leading references on the transition states of the dioxirane- mediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. R. Liu, J.; DeMello, N. C., Condroski, K R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11311
    • Yang, D.1    Wang, X.-C.2    Wong, M.-K.3    Yip, Y.-C.4    Tang, M.-W.5
  • 37
    • 0030669437 scopus 로고    scopus 로고
    • For leading references on the transition states of the dioxirane- mediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. R. Liu, J.; DeMello, N. C., Condroski, K R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10147
    • Houk, K.R.1    Liu, J.2    Demello, N.C.3    Condroski, K.R.4
  • 38
    • 0001437107 scopus 로고    scopus 로고
    • For leading references on the transition states of the dioxirane- mediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. R. Liu, J.; DeMello, N. C., Condroski, K R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12982
    • Jenson, C.1    Liu, J.2    Houk, K.N.3    Jorgensen, W.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.