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Issue 92, 2016
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SmCpR2-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols

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Abstract

A highly regio- and diastereoselective cross-coupling of allyl/propargyl ethers and δ-ketoesters, mediated by SmCpR2 reagents, delivers decorated δ-lactones. Screening of the Cp ligands on Sm(II) was employed to achieve high regio and diastereocontrol in some cases. Crucially, SmI2 gave unsatisfactory results in the transformation. The process has been exploited in a telescoped approach to complex cycloheptanols in which two Sm(II) reagents act in turn on the simple starting materials.

Graphical abstract: SmCpR2-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols

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Publication details

The article was received on 07 Sep 2016, accepted on 25 Oct 2016 and first published on 25 Oct 2016


Article type: Communication
DOI: 10.1039/C6CC07318B
Citation: Chem. Commun., 2016,52, 13503-13506
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    SmCpR2-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols

    M. P. Plesniak, X. Just-Baringo, F. Ortu, D. P. Mills and D. J. Procter, Chem. Commun., 2016, 52, 13503
    DOI: 10.1039/C6CC07318B

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