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Diastereoselective Ring-Rearrangement Metathesis to Set the Stereochemistry of All-Carbon Quaternary Centres

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posted on 03.12.2013 by Jingwei Li, Daesung Lee
A highly diastereoselective ring-rearrangement metathesis of cyclopentene derivatives containing all-carbon quaternary centres is reported. This tandem metathesis process provides cyclohexenes derivatives with two contiguous stereogenic centres, one of which is an all-carbon quaternary stereogenic centre, in high yields and excellent diastereoselecitivity. The efficacy of this methodology is showcased in the total synthesis of spiropiperidine alkaloid nitramine. In the meantime, it has been found that metathesis of the corresponding acyclic triene derivatives affords the same products with the same level of efficiency and diastereoselectivity.

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Post print version of article may differ from published version. The definitive version is available through Royal Society of Chemistry at DOI:10.1039/c2sc20812a

Publisher

Royal Society of Chemistry

Language

en_US

issn

2041-6520

Issue date

01/11/2012

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