메뉴 건너뛰기




Volumn 5, Issue 20, 2003, Pages 3767-3769

Enantioselective cyclization of alkene radical cations

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZENE; NITROALKANE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; RADICAL;

EID: 0142011097     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035564x     Document Type: Article
Times cited : (34)

References (27)
  • 4
    • 0000506428 scopus 로고
    • β-(Sulfonatoxy)alkyl radicals behave analogously: (a) Koltzenburg, G.; Behrens, G.; Schulte-Frohlinde, D. J. Am. Chem. Soc. 1982, 104, 7311-7312. (b) Crich, D.; Filzen, G. F. Tetrahedron Lett. 1993, 34, 3225-3226. (c) Taxil, E.; Bagnol, L.; Horner, J. H. Newcomb, M. Org. Lett. 2003, 5, 827-830. (d). Lancelot, S. F.; Cozens, F. L.; Schepp, N. P. Org. Biomol. Chem. 2003, 1, 1972-1979.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7311-7312
    • Koltzenburg, G.1    Behrens, G.2    Schulte-Frohlinde, D.3
  • 5
    • 0027238153 scopus 로고
    • β-(Sulfonatoxy)alkyl radicals behave analogously: (a) Koltzenburg, G.; Behrens, G.; Schulte-Frohlinde, D. J. Am. Chem. Soc. 1982, 104, 7311-7312. (b) Crich, D.; Filzen, G. F. Tetrahedron Lett. 1993, 34, 3225-3226. (c) Taxil, E.; Bagnol, L.; Horner, J. H. Newcomb, M. Org. Lett. 2003, 5, 827-830. (d). Lancelot, S. F.; Cozens, F. L.; Schepp, N. P. Org. Biomol. Chem. 2003, 1, 1972-1979.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3225-3226
    • Crich, D.1    Filzen, G.F.2
  • 6
    • 0038698180 scopus 로고    scopus 로고
    • β-(Sulfonatoxy)alkyl radicals behave analogously: (a) Koltzenburg, G.; Behrens, G.; Schulte-Frohlinde, D. J. Am. Chem. Soc. 1982, 104, 7311-7312. (b) Crich, D.; Filzen, G. F. Tetrahedron Lett. 1993, 34, 3225-3226. (c) Taxil, E.; Bagnol, L.; Horner, J. H. Newcomb, M. Org. Lett. 2003, 5, 827-830. (d). Lancelot, S. F.; Cozens, F. L.; Schepp, N. P. Org. Biomol. Chem. 2003, 1, 1972-1979.
    • (2003) Org. Lett. , vol.5 , pp. 827-830
    • Taxil, E.1    Bagnol, L.2    Horner, J.H.3    Newcomb, M.4
  • 7
    • 0038603008 scopus 로고    scopus 로고
    • β-(Sulfonatoxy)alkyl radicals behave analogously: (a) Koltzenburg, G.; Behrens, G.; Schulte-Frohlinde, D. J. Am. Chem. Soc. 1982, 104, 7311-7312. (b) Crich, D.; Filzen, G. F. Tetrahedron Lett. 1993, 34, 3225-3226. (c) Taxil, E.; Bagnol, L.; Horner, J. H. Newcomb, M. Org. Lett. 2003, 5, 827-830. (d). Lancelot, S. F.; Cozens, F. L.; Schepp, N. P. Org. Biomol. Chem. 2003, 1, 1972-1979.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 1972-1979
    • Lancelot, S.F.1    Cozens, F.L.2    Schepp, N.P.3
  • 8
    • 0002025512 scopus 로고    scopus 로고
    • Mattay, J., Ed.; Springer: Berlin
    • For classical oxidative approaches to alkene radical cations from alkenes themselves, see: (a) Hintz, S.; Heidbreder, A.; Mattay, J. In Topics in Current Chem; Mattay, J., Ed.; Springer: Berlin, 1996; Vol. 177, p 77. (b) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371-378. (c) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550-2589.
    • (1996) Topics in Current Chem , vol.177 , pp. 77
    • Hintz, S.1    Heidbreder, A.2    Mattay, J.3
  • 9
    • 0344901362 scopus 로고
    • For classical oxidative approaches to alkene radical cations from alkenes themselves, see: (a) Hintz, S.; Heidbreder, A.; Mattay, J. In Topics in Current Chem; Mattay, J., Ed.; Springer: Berlin, 1996; Vol. 177, p 77. (b) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371-378. (c) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550-2589.
    • (1987) Acc. Chem. Res. , vol.20 , pp. 371-378
    • Bauld, N.L.1    Bellville, D.J.2    Harirchian, B.3    Lorenz, K.T.4    Pabon, R.A.5    Reynolds, D.W.6    Wirth, D.D.7    Chiou, H.-S.8    Marsh, B.K.9
  • 10
    • 0031573815 scopus 로고    scopus 로고
    • For classical oxidative approaches to alkene radical cations from alkenes themselves, see: (a) Hintz, S.; Heidbreder, A.; Mattay, J. In Topics in Current Chem; Mattay, J., Ed.; Springer: Berlin, 1996; Vol. 177, p 77. (b) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371-378. (c) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550-2589.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2550-2589
    • Schmittel, M.1    Burghart, A.2
  • 12
    • 0001271574 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim
    • (b) Crich, D. In Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 188-206.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 188-206
    • Crich, D.1
  • 16
    • 0001160683 scopus 로고    scopus 로고
    • (b) Crich, D.; Neelamkavil, S. Org. Lett. 2002, 4, 2573-2575. (c) Crich, D.; Ranganathan, K.; Neelamkavil, S.; Huang, X. J. Am. Chem. Soc. 2003, 125, 7942-7947.
    • (2002) Org. Lett. , vol.4 , pp. 2573-2575
    • Crich, D.1    Neelamkavil, S.2
  • 24
    • 0142036663 scopus 로고    scopus 로고
    • note
    • Enantioselectivities of radical precurosors and of products were assigned by GC and/or HPLC, as appropriate, over chiral stationary phases that demonstrated baseline resolution of the corresponding racemic materials.
  • 27
    • 0142036662 scopus 로고    scopus 로고
    • note
    • 4e,7b however, of diastereoselective attack of alcohols on alkene radical cations in similarly generated radical ionic contact ion pairs when the counterion is the weaker nucleofuge, diethyl phosphate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.