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Synlett 2000; 2000(9): 1315-1317
DOI: 10.1055/s-2000-7127
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Ruthenium-Catalysed Addition of Carboxylic Acids onto 1-Ethoxy-2-ethynylcyclopropane to Yield Functional Allenes with Skeletal Rearrangement

Ingo Emme* , Christian Bruneau, Armin de Meijere, Pierre H. Dixneuf
  • *Laboratoire de Chimie de Coordination et Catalyse, UMR 6509: CNRS - Université de Rennes, Campus de Beaulieu, F-35042 Rennes, France; Fax 33 (0)2 99 28 69 39; E-mail: pierre.dixneuf@univ-rennes1.fr; christian.bruneau@univ-rennes1.fr
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Publication Date:
31 December 2000 (online)

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The selective one-step transformation of trans-1-ethoxy-2-ethynylcyclopropane (1) by a formal 1,4-addition of carboxylic acids with cyclopropyl-ring opening into allene derivatives 4a-i (53-96% yield) is achieved with the binuclear ruthenium precatalyst [Ru(O2CH)(CO)2(PPh3)]2. The products combine a reactive allene moiety and a protected aldehyde functionality, and thus offer themselves as versatile building blocks for organic synthesis.

cyclopropanes - ruthenium catalysis - ring-opening reactions - allenes - aldehydes

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