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Issue 20, 2018
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Asymmetric synthesis of multiple quaternary stereocentre-containing cyclopentyls by oxazolidinone-promoted Nazarov cyclizations

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Abstract

Carbometalation of oxazolidinone (Ox)-substituted ynamides is used to generate highly substituted Ox-divinyl (and aryl vinyl) ketones for use in Nazarov cyclizations. The Ox-group serves as a remarkably effective chiral activating group, enabling the torquoselective Nazarov cyclization of these sterically congested substrates to be performed under mild conditions. It also serves as a charge-stabilizing group in the intermediate oxyallyl cation, suppressing undesired [1,2]-sigmatropic shifts of neighboring substituents and facilitating the regio- and stereoselective incorporation of nucleophiles to yield cyclopentanoids containing up to three contiguous all-carbon quaternary (4°) stereocentres.

Graphical abstract: Asymmetric synthesis of multiple quaternary stereocentre-containing cyclopentyls by oxazolidinone-promoted Nazarov cyclizations

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Publication details

The article was received on 04 Jan 2018, accepted on 19 Apr 2018 and first published on 20 Apr 2018


Article type: Edge Article
DOI: 10.1039/C8SC00031J
Chem. Sci., 2018,9, 4644-4649
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    Asymmetric synthesis of multiple quaternary stereocentre-containing cyclopentyls by oxazolidinone-promoted Nazarov cyclizations

    R. Volpe, R. J. Lepage, Jonathan M. White, E. H. Krenske and B. L. Flynn, Chem. Sci., 2018, 9, 4644
    DOI: 10.1039/C8SC00031J

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