Issue 19, 2014

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

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

Supplementary files

Article information

Article type
Communication
Submitted
22 Nov 2013
Accepted
11 Dec 2013
First published
12 Dec 2013
This article is Open Access
Creative Commons BY license

Chem. Commun., 2014,50, 2518-2521

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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