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Synfacts 2011(7): 0722-0722  
DOI: 10.1055/s-0030-1260514
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2,3,5-Trisubstituted Furans from Cyclopropenyl-1,1-Dicarboxylates

Contributor(s): Victor Snieckus, Johnathan Board
J. Chen, S. Ni, S. Ma*
Shanghai Institute of Organic Chemistry and East China Normal University, Shanghai, P. R. of China
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Publikationsdatum:
17. Juni 2011 (online)

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Significance

Reported is the synthesis of substituted furans through the phosphine-catalyzed opening and intramolecular cyclization of 2-cyclopropene-1,1-dicarboxylic acid dimethylesters. Although cyclopropenes have been opened with a variety of different metal catalysts, this appears to be the first time it has been achieved using organocatalysis. The starting cyclopropenes can be made by reaction of methyldiazomalonate and alkynes using rhodium(II) acetate catalysis.