Stereoselective Synthesis of 2Z,4E-Configured Dienoates through Tethered Ring Closing Metathesis

Bernd Schmidt; Stephan Audörsch; Oliver Kunz

doi:10.1055/s-0035-1562536

Synthesis, Table of Contents

Synthesis 2016; 48(24): 4509-4518
DOI: 10.1055/s-0035-1562536

paper

Stereoselective Synthesis of 2Z,4E-Configured Dienoates through Tethered Ring Closing Metathesis

Authors

Bernd Schmidt*

Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam-Golm, Germany Email: bernd.schmidt@uni-potsdam.de
Stephan Audörsch

Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam-Golm, Germany Email: bernd.schmidt@uni-potsdam.de
Oliver Kunz

Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam-Golm, Germany Email: bernd.schmidt@uni-potsdam.de

Abstract

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Abstract

A two-step sequence leading from racemic allylic alcohols and vinylacetic acid to ethyl (2Z,4E)-dienoates is described. The sequence involves Steglich esterification of the reactants, followed by a one-pot ring closing metathesis–base induced elimination–alkylation reaction to furnish the products in high stereoselectivity. Trapping of the intermediate sodium carboxylates is accomplished efficiently using Meerwein’s salt Et₃OBF₄.

Key words

allyl alcohols - dienes - ring closing metathesis - ruthenium - elimination

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References

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