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Issue 19, 2017
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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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Supplementary files

Article information


Submitted
25 Mar 2017
Accepted
11 Apr 2017
First published
12 Apr 2017

Org. Biomol. Chem., 2017,15, 4159-4164
Article type
Paper

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, 15, 4159
DOI: 10.1039/C7OB00739F

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