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Synlett 1994; 1994(12): 1007-1008
DOI: 10.1055/s-1994-34978
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Regioselective Synthesis of 1,2,3,5-Substituted Pyrroles from Conjugated Enamines and 1,1-Dibromo-3-Phenyl-1-Butene

Herbert Frey*
  • *Organische Chemie, FB Chemie, Carl v. Ossietzky Universität Oldenburg, Postfach 2503, D-26015 Oldenburg, Germany
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Publication Date:
22 March 2002 (online)

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A new [3 + 2] annulation to 1,2,3,5-substituted pyrroles starting from conjugated enamines and 1,1-dibromo-3-phenyl-1-butene upon treating with KO-t-Bu in THF in a single step is reported. The reaction proceeds via dehydrobromination, SN2′-substitution and a tandem aza-Claisen rearrangement - cyclization reaction.