Issue 19, 2017
From the journal:

Organic & Biomolecular Chemistry

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

Huan-Ming Huang, ORCID logo a   Pablo Bonillaa  and  David J. Procter ORCID logo *a  

* Corresponding authors

a School of Chemistry, University of Manchester, Oxford Road, Manchester, UK
E-mail: david.j.procter@manchester.ac.uk
Fax: +44 (0)161 2754939
Tel: +44 (0)161 2751425

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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Article information

DOI
https://doi.org/10.1039/C7OB00739F
Article type
Paper
Submitted
25 Mar 2017
Accepted
11 Apr 2017
First published
12 Apr 2017

Org. Biomol. Chem., 2017,15, 4159-4164

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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, 15, 4159 DOI: 10.1039/C7OB00739F

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