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Issue 19, 2014
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Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides

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Abstract

Structural characterisation and reactivity of new tetrahedral intermediates based on a highly modular barbituric acid scaffold, formed via chemoselective electron transfer using the SmI2–H2O reagent, are reported. Lewis acid promoted cleavage of bicyclic α-amino alcohols affords vinylogous N-acyliminium ions, which undergo selective (>95 : 5, 1,4 over 1,2) capture with a suite of diverse nucleophiles in a practical sequence to biologically active uracil derivatives.

Graphical abstract: Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides

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Supplementary files

Article information


Submitted
22 Nov 2013
Accepted
11 Dec 2013
First published
12 Dec 2013

This article is Open Access

Chem. Commun., 2014,50, 2518-2521
Article type
Communication

Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides

M. Szostak, B. Sautier and D. J. Procter, Chem. Commun., 2014, 50, 2518
DOI: 10.1039/C3CC48932A

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