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Synlett 1996; 1996(3): 218-220
DOI: 10.1055/s-1996-5368
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New Synthesis of Heterocycles via Palladium-Catalyzed Double Carbonylation of Cyclic Alk-1-ynyl Carbonates

Christophe Darcel* , Christian Bruneau1 , Pierre H. Dixneuf1
  • *Laboratoire de Chimie de Coordination Organique, URA CNRS 415, Campus de Beaulieu, Université de Rennes, F-35042 Rennes, France
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Publication Date:
31 December 2000 (online)

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Carbonylation of cyclic alkynyl carbonates in the presence of a palladium(0) catalyst gives functional 5-hydroxyalka-2,3-dienoates in one step via zwitterionic allenylpalladium intermediates. From 3-en-1-ynyl cyclic carbonates, double vicinal carbonylation takes place to selectively afford oxolenones or 4-oxabicyclo[4.3.0]-nona-5,9-dien-2,7-diones.

palladium catalysis - carbonylation - allenes - oxolenones - heterobicycles - cyclic alkynyl carbonates