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Synlett 1996; 1996(3): 215-217
DOI: 10.1055/s-1996-5380
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Asymmetric Synthesis of Substituted Functionalized Cis and Trans Vinylcyclopropanes via Palladium Catalyzed Reactions

V. Michelet, I. Besnier, J. P. Genêt*
  • *Ecole Nationale Supérieure de Chimie de Paris, Laboratoire de Synthèse Organique, Associé au CNRS, 11 rue Pierre et Marie Curie, F-75231 Paris Cedex 05, France, Fax (1) 44 07 10 62, Bitnet genet@ext.jussieu.fr
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Publication Date:
31 December 2000 (online)

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A facile method for synthesizing trans and cis disubstituted vinylic cyclopropanes is described. The key steps are alkylation of chiral allylic alcohols and cyclisation via SN of functionalized allylic substrates using palladium (0) catalyst with high regio- and stereoselectivity.

alkylation - chiral allylic alcohol - intramolecular SN’ - palladium catalyst - chirality transfer - chiral cyclopropanes