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Synlett 1993; 1993(12): 905-906
DOI: 10.1055/s-1993-22646
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Regioselective Synthesis of 2,4-, 2,5-, and 2,4,5-Substituted Furans from Aldehydes or Ketones and 1,1-Dibromo-3-phenyl-1-butene

Herbert Frey*
  • *Organische Chemie, FB Chemie, Carl v. Ossietzky Universität, Postfach 2503, D-26015 Oldenburg, Germany
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Publication History

Publication Date:
19 March 2002 (online)

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A new [ 3 + 2] annulation to 2,4-, 2.5-, and 2,4,5 - substituted furans (15 examples) starting from aldehydes or ketones and 1,1-dibromo-3-phenyl-1-butene upon treating with KO-t-Bu in THF in a single step is developed. The reaction proceeds via dehydrobromination, SN2′ - substitution, and a tandem Claisen rearrangement - cyclization reaction.

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