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Volumn 69, Issue 20, 2004, Pages 6860-6866

Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones

Author keywords

[No Author keywords available]

Indexed keywords

BORON COMPOUNDS; CATALYSIS; CATALYSTS; ELECTRONIC STRUCTURE; FREE ENERGY; TOLUENE;

EID: 4644223892     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048959i     Document Type: Article
Times cited : (58)

References (59)
  • 2
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    • For recent reviews, see: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504. (b) Singh, V. K. Synthesis 1992, 605-617. (c) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (d) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1475-1504
    • Wallbaum, S.1    Martens, J.2
  • 3
    • 0026663693 scopus 로고
    • For recent reviews, see: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504. (b) Singh, V. K. Synthesis 1992, 605-617. (c) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (d) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
    • (1992) Synthesis , pp. 605-617
    • Singh, V.K.1
  • 4
    • 0342697384 scopus 로고
    • For recent reviews, see: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504. (b) Singh, V. K. Synthesis 1992, 605-617. (c) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (d) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
    • (1993) Chem. Rev. , vol.93 , pp. 763-784
    • Deloux, L.1    Srebnik, M.2
  • 5
    • 0032541271 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504. (b) Singh, V. K. Synthesis 1992, 605-617. (c) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (d) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1986-2012
    • Corey, E.J.1    Helal, C.J.2
  • 54
    • 4644330618 scopus 로고    scopus 로고
    • note
    • 2 will become lower. Reference 19 gives 0.06 of the σ value for the MeS group. However, on the basis of our experimental results, the σ value of the MeS group should be suggested as -0.51, which is an average of the σ values calculated from Figures 2 and 4 because substituted propiophenones show good linearities in the Hammett plots.


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