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Issue 61, 2014
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Mechanistic investigation of the selective reduction of Meldrum's acids to β-hydroxy acids using SmI2 and H2O

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Abstract

The mechanism of a recently reported first mono-reduction of cyclic 1,3-diesters (Meldrum's acids) to β-hydroxy acids with SmI2–H2O has been studied using a combination of reactivity, deuteration, kinetic isotope and radical clock experiments. Most crucially, the data indicate that the reaction proceeds via reversible electron transfer and that water, as a ligand for SmI2, stabilizes the radical anion intermediate rather than only promoting the first electron transfer as originally proposed.

Graphical abstract: Mechanistic investigation of the selective reduction of Meldrum's acids to β-hydroxy acids using SmI2 and H2O

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Supplementary files

Article information


Submitted
30 Apr 2014
Accepted
05 Jun 2014
First published
05 Jun 2014

This article is Open Access

Chem. Commun., 2014,50, 8391-8394
Article type
Communication

Mechanistic investigation of the selective reduction of Meldrum's acids to β-hydroxy acids using SmI2 and H2O

M. Szostak, S. E. Lyons, M. Spain and D. J. Procter, Chem. Commun., 2014, 50, 8391
DOI: 10.1039/C4CC03216K

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