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Synthesis 2016; 48(24): 4509-4518
DOI: 10.1055/s-0035-1562536
DOI: 10.1055/s-0035-1562536
paper
Stereoselective Synthesis of 2Z,4E-Configured Dienoates through Tethered Ring Closing Metathesis
Further Information
Publication History
Received: 14 June 2016
Accepted after revision: 19 July 2016
Publication Date:
31 August 2016 (online)
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562536.
- Supporting Information
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