Synlett 2014; 25(5): 693-695
DOI: 10.1055/s-0033-1340496
letter
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Formation of (E)-β-Alkoxy Acrylates from Fischer Carbene Complexes and Chelated Amino Acid Ester Enolates

Authors

  • Rupsha Chaudhuri

    Institut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany   Fax: +49(681)3022409   Email: u.kazmaier@mx.uni-saarland.de
  • Uli Kazmaier*

    Institut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany   Fax: +49(681)3022409   Email: u.kazmaier@mx.uni-saarland.de
Further Information

Publication History

Received: 29 October 2013

Accepted after revision: 06 December 2013

Publication Date:
13 January 2014 (online)


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Abstract

Chelated amino acid ester enolates react with alkyl Fischer carbene complexes via nucleophilic attack on the electrophilic carbene center. Subsequent elimination of the metal fragment and trifluoroacetamide results in the formation of β-alkoxy-α,β-­unsaturated esters in a highly E-stereoselective fashion.

Supporting Information