SmCpR 2-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols

Mateusz Plesniak; Xavier Just-Baringo; Fabrizio Ortu; David Mills; David Procter

doi:10.1039/C6CC07318B

SmCp^R ₂-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols

Mateusz Plesniak, Xavier Just-Baringo, Fabrizio Ortu, David Mills, David Procter

Research output: Contribution to journal › Article › peer-review

Abstract

A highly regio- and diastereoselective cross-coupling of allyl/propargyl ethers and δ-ketoesters, mediated by SmCp^R₂ 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.

Original language	English
Pages (from-to)	13503-13506
Number of pages	4
Journal	Chemical Communications
Volume	52
DOIs	https://doi.org/10.1039/C6CC07318B
Publication status	Published - 10 Nov 2016

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title = "SmCpR 2-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols",

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.",

author = "Mateusz Plesniak and Xavier Just-Baringo and Fabrizio Ortu and David Mills and David Procter",

year = "2016",

month = nov,

day = "10",

doi = "10.1039/C6CC07318B",

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T1 - SmCpR 2-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols

AU - Plesniak, Mateusz

AU - Just-Baringo, Xavier

AU - Ortu, Fabrizio

AU - Mills, David

AU - Procter, David

PY - 2016/11/10

Y1 - 2016/11/10

N2 - 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.

AB - 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.

U2 - 10.1039/C6CC07318B

DO - 10.1039/C6CC07318B

M3 - Article

SN - 1359-7345

VL - 52

SP - 13503

EP - 13506

JO - Chemical Communications

JF - Chemical Communications

ER -

SmCpR 2-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols

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SmCp^R ₂-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols