Synlett 2014; 25(20): 2957-2961
DOI: 10.1055/s-0034-1378905
letter
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Enantioselective Approach to Spirocyclic Δβ,γ-Butenolides

Authors

  • Joanna Hejmanowska

    Institute of Organic Chemistry, Department of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland   Email: lukasz.albrecht@p.lodz.pl
  • Marek Dzięgielewski

    Institute of Organic Chemistry, Department of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland   Email: lukasz.albrecht@p.lodz.pl
  • Dorota Kowalczyk

    Institute of Organic Chemistry, Department of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland   Email: lukasz.albrecht@p.lodz.pl
  • Łukasz Albrecht*

    Institute of Organic Chemistry, Department of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland   Email: lukasz.albrecht@p.lodz.pl
Further Information

Publication History

Received: 27 August 2014

Accepted after revision: 02 October 2014

Publication Date:
18 November 2014 (online)


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Abstract

A novel method for the preparation of the spirocyclic Δβ,γ-butenolides is presented. The developed strategy is based on a trienamine-mediated [4+2]-cycloaddition between (E)-3-alkylidene-5-arylfuran-2(3H)-ones and 2,4-dienals. Target products containing three contiguous centres including one quaternary are efficiently formed in a highly enantiomerically enriched form in the presence of the silyl-protected diphenylprolinol aminocatalyst.