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Tytuł artykułu

Asymmetric Synthesis of Multi-substituted Indolizidines by Intramolecular Addition of Allylsilane to Chiral 2,3-Dihydro-4-pyridones

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A short and synthetically attractive asymmetric synthesis of substituted indolizidines is described. The discovered reaction sequence consists of the asymmetric aza-Diels-Alder reaction of aldimines with Danishefsky's diene and the intramolecular Hosomi-Sakurai allylation. The absolute configuration of cycloadducts was established by CD-spectroscopy
Rocznik
Strony
1919--1928
Opis fizyczny
Bibliogr. 23 poz.
Twórcy
autor
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 02-224 Warsaw, Poland
autor
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 02-224 Warsaw, Poland
autor
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 02-224 Warsaw, Poland
autor
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 02-224 Warsaw, Poland
Bibliografia
  • 1.Comins D.L. and Joseph S.P., In Advances in Nitrogen Heterocycles; Moody C.J. Ed., JAI Press, Inc.: Greenwich CT, Vol. 2, pp 251-294 (1996).
  • 2.Comins D.L., Joseph S.P. and Goehring R.R., J. Am. Chem. Soc., 116,4719 (1994).
  • 3.(a) Davies S.G. and Ishihara O., Tetrahedron: Asymmetry, 2,183 (1991); (b) Davies S.G., Ishihara O. ar Walters I.A.S.,J. Chem. Soc., Perkin Trans. 1, 1141 (1994).
  • 4.Kervin J.F., Jr. and Danishefsky S., Tetrahedron Lett., 23, 3739 (1982).
  • 5.Ratni H. and Kündig E.P., Org. Lett., 1, 1997 (1999).
  • 6.Hattori K. and Yamamoto H., Tetrahedron, 49, 1749 (1993).
  • 8.Hattori K. and Yamamoto H., Synlett, 129 (1993).
  • 9.(a) Kunz H. and Pfrengle W., Angew. Chem. Int. Ed. Engl., 2$, 1067(1989); (b)Pfrengle W. and Kunz 1 J. Org. Chem., 54,4261 (1989); (c) Weymann W., Pfrengle W., Schollmeyer D. and Kunz H., Synthes, 1151 (1997); (d) Zech G. and Kunz H., Angew. Chem. Int. Ed. Engl., 42, 787 (2003).
  • 10.(a) Midland M.M. and Koops R.W,,J. Org. Chem., 57, 1158 (1992); (b) Devine P.N., Reilly M. andC T., Tetrahedron Lett., 34, 5827 (1993).
  • 11.(a) Larsen S.D. and Grieco P.A., J. Am. Chem. Soc., 107,1768 (1985); (b) Waldmann H., Braun M. a Dräger M., A ngew. Chem. Int. Ed. Engl., 29, 1468 (1990); (c) Waldmann H. and Braun M., J Org. Chem., 57,4444(1992); (d) Waldmann H., Synlett, 133 (1995); (e) Lock R. and Waldmann H., Tetrahedron Lett., 37, 2753(1996).
  • 12.(a) Hattori K. and Yamamoto H., J. Org. Chem., 57, 3264 (1992); (b) Ishihara K., Miyata M., Hattori K., Tada T. and Yamamoto H., J. Am. Chem. Soc., 116, 10520 (1994).
  • 13.Kobayashi S., Komiyama S. and Ishitani H., Angev. Chem. Int. Ed. Engl., 37, 979 (1998).
  • 14.(a) Yao S., Johannsen M., Hazell R.G. and Jargensen K.A., Angew. Chem. Int. Ed. Engl., 37, 31 (1998); (b) Yao S., Saaby S., Hazell R.G. and Jargensen K.A., Chem. Eur. J., 6, 2435 (2000).
  • 15.Daly J.W., Garraffo H.M. and Spande T.F., In The Alkaloids; Cordell G.A., (Ed.); Academic Press: San Diego, CA, Vol. 43, pp 185-288 (1993).
  • 16.Comins D.L. and Zhang Y., J. Am. Chem. Soc., 118, 12248(1996).
  • 17.Furman B. and Dziedzic M., Tetrahedron Lett., 44, 6629 (2003).
  • 19.Other chiral Lewis acids such as BINAP-Cuor BINOL-Zr gave the corresponding dihydropyridone good yields as racemic mixtures.
  • 20.Smith H.E., Application of the benzene sector and benzene chirality roles. In Circular Dichroism Principles and Applications ; Nakanishi K., Berova N. and Woody R.W., (Eds.); VSH Publishers: New Y< pp. 397-429 (2000).
  • 21.Lightner D.A., The octant rule. In Circular Dichroism Principles and Applications; Nakanishi Berova N. and Woody R.W., (Eds.); VSH Publishers: New York, pp. 261-303 (2000).
  • 22.AllingerN.L. and Tribble M.T., Tetrahedron, 28,1191 (1972); b) Lo Cicero B., Weisbuch F. and Dan J. Org. Chem., 46, 914 (1981).
  • 23.Fontana L.P. and Smith H.E., J. Org. Chem., 52, 3386 (1987).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0003-0011
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