Synlett 2012; 23(6): 851-854
DOI: 10.1055/s-0031-1290488
letter
© Georg Thieme Verlag Stuttgart · New York

α,β-Unsaturated δ-Valerolactones through RCM–Isomerization Sequence

Bernd Schmidt*
Universität Potsdam, Institut für Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24-25, 14476 Potsdam-Golm, Germany, Fax: +49(331)9775059   Email: bernd.schmidt@uni-potsdam.de
,
Oliver Kunz
Universität Potsdam, Institut für Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24-25, 14476 Potsdam-Golm, Germany, Fax: +49(331)9775059   Email: bernd.schmidt@uni-potsdam.de
› Author Affiliations
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Publication History

Received: 11 January 2012

Accepted after revision: 03 February 2012

Publication Date:
16 March 2012 (online)


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Abstract

α,β-Unsaturated δ-lactones are accessible via a sequential ring-closing metathesis (RCM) double-bond migration reaction starting from butenoates of allyl alcohols. This approach proceeds efficiently with lower catalyst loadings and higher initial substrate concentrations compared to the alternative RCM of acrylates derived from homoallylic alcohols.

Supporting Information