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Volumn 10, Issue 17, 2008, Pages 3887-3890

Michael addition of allenoates to electron-deficient olefins: Facile synthesis of 2-alkynyl-substituted glutaric acid derivatives

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EID: 60949108432     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801411b     Document Type: Article
Times cited : (31)

References (32)
  • 1
    • 0003573894 scopus 로고
    • For selected recent reviews on conjugate addition reactions, see: a, Pergamon: Oxford, UK
    • For selected recent reviews on conjugate addition reactions, see: (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, UK, 1992.
    • (1992) Conjugate Addition Reactions in Organic Synthesis
    • Perlmutter, P.1
  • 9
    • 4544320494 scopus 로고    scopus 로고
    • For the generation and reaction of allenyl/propargyl anions, see: a, Krause, N, Hashmi, A. S. K, Eds, Wiley-VCH: Weinheim, Germany, Chapter 9
    • For the generation and reaction of allenyl/propargyl anions, see: (a) Marshall, J. A.; Gung, B. W.; Grachan, M. L. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, Chapter 9.
    • (2004) Modern Allene Chemistry , vol.1
    • Marshall, J.A.1    Gung, B.W.2    Grachan, M.L.3
  • 10
    • 0035908165 scopus 로고    scopus 로고
    • (b) Back, T. G. Tetrahedron 2001, 57, 5263-5301.
    • (2001) Tetrahedron , vol.57 , pp. 5263-5301
    • Back, T.G.1
  • 11
  • 19
    • 10844270526 scopus 로고    scopus 로고
    • For selected recent papers on glutaric acid derivatives, see: a
    • For selected recent papers on glutaric acid derivatives, see: (a) Yan, J.; Travis, B. R.; Borhan, B. J. Org. Chem. 2004, 69, 9299-9302.
    • (2004) J. Org. Chem , vol.69 , pp. 9299-9302
    • Yan, J.1    Travis, B.R.2    Borhan, B.3
  • 22
    • 0030942410 scopus 로고    scopus 로고
    • For glutaric acid derivatives used in total synthesis, see: d
    • For glutaric acid derivatives used in total synthesis, see: (d) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982-991.
    • (1997) J. Org. Chem , vol.62 , pp. 982-991
    • Nayyar, N.K.1    Hutchison, D.R.2    Martinelli, M.J.3
  • 25
    • 0011809580 scopus 로고    scopus 로고
    • To the best of our knowledge, there is only one report on 2-alkynyl-substituted glutaric acid derivatives, see: Casara, P.; Metcalf, B. W. Tetrahedron Lett. 1978, 19, 1581-1584.
    • To the best of our knowledge, there is only one report on 2-alkynyl-substituted glutaric acid derivatives, see: Casara, P.; Metcalf, B. W. Tetrahedron Lett. 1978, 19, 1581-1584.
  • 26
    • 34547176199 scopus 로고    scopus 로고
    • For a recent example of alkynyl-substituted cyclization products from sulfonylallene derivatives by base treatment, see: (a) Kitagaki, S, Teramoto, S, Mukai, C. Org. Lett. 2007, 9, 2549-2552, and references cited therein
    • For a recent example of alkynyl-substituted cyclization products from sulfonylallene derivatives by base treatment, see: (a) Kitagaki, S.; Teramoto, S.; Mukai, C. Org. Lett. 2007, 9, 2549-2552, and references cited therein.
  • 27
    • 3042699990 scopus 로고    scopus 로고
    • For a palladium-catalyzed alkylation of vinyl oxiranes with allenoates, see: b
    • For a palladium-catalyzed alkylation of vinyl oxiranes with allenoates, see: (b) Nanayakkara, P.; Alper, H. J. Org. Chem. 2004, 69, 4686-4691.
    • (2004) J. Org. Chem , vol.69 , pp. 4686-4691
    • Nanayakkara, P.1    Alper, H.2
  • 30
    • 41649094683 scopus 로고    scopus 로고
    • It is well-known that allenic and propargylic esters tend to interconvert to each other in the presence of base through a prototropic rearrangement, see: (a) Sleeman, M. J, Meehan, G. V. Tetrahedron Lett. 1989, 30, 3345-3348
    • It is well-known that allenic and propargylic esters tend to interconvert to each other in the presence of base through a prototropic rearrangement, see: (a) Sleeman, M. J.; Meehan, G. V. Tetrahedron Lett. 1989, 30, 3345-3348.


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