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Issue 30, 2012
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A general electron transfer reduction of lactones using SmI2–H2O

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Abstract

Herein we describe a strategy for the selective, electron transfer reduction of lactones of all ring sizes and topologies using SmI2H2O and a Lewis base to tune the redox properties of the complex. The current protocol permits instantaneous reduction of lactones to the corresponding diols in excellent yields, under mild reaction conditions and with useful chemoselectivity. We demonstrate the broad utility of this transformation through the reduction of complex lactones and sensitive drug-like molecules. Sequential electron transfer reactions and syntheses of deuterated diols are also described.

Graphical abstract: A general electron transfer reduction of lactones using SmI2–H2O

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Supplementary files

Article information


Submitted
03 Jan 2012
Accepted
30 Jan 2012
First published
31 Jan 2012

Org. Biomol. Chem., 2012,10, 5820-5824
Article type
Communication

A general electron transfer reduction of lactones using SmI2–H2O

M. Szostak, K. D. Collins, N. J. Fazakerley, M. Spain and D. J. Procter, Org. Biomol. Chem., 2012, 10, 5820
DOI: 10.1039/C2OB00017B

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