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Synlett 1990; 1990(6): 359-361
DOI: 10.1055/s-1990-21095
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Novel Generation and Regio- and Stereospecific 1,3-Dipolar Cycloaddition of 2-Ethoxycarbonyl-3,3-dimethyl-3H-indolium-1-methanide

Colin W. G. Fishwick* , Andrew D. Jones, Michael B. Mitchell, Drake S. Eggleston, Paul W. Baures
  • *School of Chemistry, The University of Leeds, Leeds, West Yorkshire, LS2 9JT, England
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Publication Date:
08 March 2002 (online)

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2-Ethoxycarbonyl-3,3-dimethyl-3H-indolium-1-methanide, formed in situ from alkylation of the corresponding 3H-indole with trimethylsilylmethyl triflate followed by spontaneous desilylation, undergoes regio- and stereospecific 1,3-dipolar cycloaddition only with bis-activated electron deficient dipolarophiles. With mono-substituted dipolarophiles only the adduct resulting from the cycloaddition of intermediate ylide and 3H-indole starting material is observed.

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