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Selective construction of quaternary stereocentres in radical cyclisation cascades triggered by electron-transfer reduction of amide-type carbonyls

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Abstract

Radical–radical cyclisation cascades, triggered by single-electron-transfer to amide-type carbonyls using SmI2–H2O–LiBr, result in the selective construction of quaternary carbon stereocentres. The cascades deliver tricyclic barbiturates with four stereocentres in good yield and with excellent diastereocontrol.

Graphical abstract: Selective construction of quaternary stereocentres in radical cyclisation cascades triggered by electron-transfer reduction of amide-type carbonyls

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Publication details

The article was received on 25 Mar 2017, accepted on 11 Apr 2017 and first published on 12 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00739F
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Selective construction of quaternary stereocentres in radical cyclisation cascades triggered by electron-transfer reduction of amide-type carbonyls

    H. Huang, P. Bonilla and D. J. Procter, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00739F

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