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Volumn 129, Issue 2, 2007, Pages 292-293

Enantioselective Friedel-Crafts reaction of electron-rich alkenes catalyzed by chiral Brønsted acid

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BRONSTED ACID;

EID: 33846189422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0678166     Document Type: Article
Times cited : (317)

References (43)
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    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford, Chapter 1.8, pp
    • (a) Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 1.8, pp 293-339.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 293-339
    • Olah, G.A.1    Krishnamurti, R.2    Prakash, G.K.S.3
  • 2
    • 33846199064 scopus 로고    scopus 로고
    • Sheldon, R. A, Bekkum, H, Eds, Wiley-VCH: New York
    • (b) Meima, G. R.; Lee, G. S.; Garces, J. M. In Friedel-Crafts Alkylation; Sheldon, R. A., Bekkum, H., Eds.; Wiley-VCH: New York, 2001; pp 151-160.
    • (2001) Friedel-Crafts Alkylation , pp. 151-160
    • Meima, G.R.1    Lee, G.S.2    Garces, J.M.3
  • 3
    • 0037680718 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Jørgensen, K. A. Synthesis 2003, 1117-1125.
    • (2003) Synthesis , pp. 1117-1125
    • Jørgensen, K.A.1
  • 12
    • 0346865819 scopus 로고    scopus 로고
    • For reviews on chiral Brønsted acid catalysis, see: a
    • For reviews on chiral Brønsted acid catalysis, see: (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289-296.
    • (2003) Chem. Soc. Rev , vol.32 , pp. 289-296
    • Schreiner, P.R.1
  • 39
    • 33846223771 scopus 로고    scopus 로고
    • Presented at the 86th Annual Meeting of the Chemical Society of Japan, March 27-30, 2006; Abstract No. 2H5-17.
    • Presented at the 86th Annual Meeting of the Chemical Society of Japan, March 27-30, 2006; Abstract No. 2H5-17.
  • 41
    • 0000962345 scopus 로고
    • For a review on the classification of dipolar aprotic solvents, see
    • For a review on the classification of dipolar aprotic solvents, see: Kolthoff, I. M. Anal. Chem. 1974, 46, 1992-2003.
    • (1974) Anal. Chem , vol.46 , pp. 1992-2003
    • Kolthoff, I.M.1
  • 42
    • 33750366006 scopus 로고    scopus 로고
    • During the preparation of this manuscript, Kobayashi, et al. reported the metal salt-catalyzed Mannich reaction of 1,3-dicarbonyl compounds with enecarbamates as an aliphatic imine surrogate, see: Kobayashi, S.; Gustafsson, T.; Shimizu, Y.; Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8, 4923-4925.
    • During the preparation of this manuscript, Kobayashi, et al. reported the metal salt-catalyzed Mannich reaction of 1,3-dicarbonyl compounds with enecarbamates as an aliphatic imine surrogate, see: Kobayashi, S.; Gustafsson, T.; Shimizu, Y.; Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8, 4923-4925.
  • 43
    • 33846241589 scopus 로고    scopus 로고
    • Imine (5) was completely isomerized to enecarbamate (3b) during distillation, and hence it can be considered that enecarbametes (3) serve as stable and useful precursors of aliphatic imines in the present activation mode. (Diagram presented).
    • Imine (5) was completely isomerized to enecarbamate (3b) during distillation, and hence it can be considered that enecarbametes (3) serve as stable and useful precursors of aliphatic imines in the present activation mode. (Diagram presented).


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