Selective reductions of cyclic 1,3-diesters using SmI2 and H2O

Giuditta Guazzelli; Sara De Grazia; Karl D. Collins; Hiroshi Matsubara; Malcolm Spain; David J. Procter

doi:10.1021/ja901715d

Selective reductions of cyclic 1,3-diesters using SmI2 and H2O

Giuditta Guazzelli, Sara De Grazia, Karl D. Collins, Hiroshi Matsubara, Malcolm Spain, David J. Procter

Research output: Contribution to journal › Article › peer-review

Abstract

(Chemical Equation Presented) SmI2?H2O reduces cyclic 1,3-diesters to 3-hydroxyacids with no over-reduction. Furthermore, the reagent system is selective for cyclic 1,3-diesters over acyclic 1,3-diesters and esters. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron transfer to the ester carbonyl and the anomeric stabilization of the resulting radical-anion intermediate. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. Copyright © 2009 American Chemical Society.

Original language	English
Pages (from-to)	7214-7215
Number of pages	1
Journal	Journal of the American Chemical Society
Volume	131
Issue number	21
DOIs	https://doi.org/10.1021/ja901715d
Publication status	Published - 3 Jun 2009

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10.1021/ja901715d

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CCDC 721800: Experimental Crystal Structure Determination
Guazzelli, G. (Contributor), De Grazia, S. (Contributor), Collins, K. D. (Contributor), Matsubara, H. (Contributor), Spain, M. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2010
DOI: 10.5517/ccs72wy, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccs72wy&sid=DataCite
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title = "Selective reductions of cyclic 1,3-diesters using SmI2 and H2O",

abstract = "(Chemical Equation Presented) SmI2?H2O reduces cyclic 1,3-diesters to 3-hydroxyacids with no over-reduction. Furthermore, the reagent system is selective for cyclic 1,3-diesters over acyclic 1,3-diesters and esters. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron transfer to the ester carbonyl and the anomeric stabilization of the resulting radical-anion intermediate. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. Copyright {\textcopyright} 2009 American Chemical Society.",

author = "Giuditta Guazzelli and {De Grazia}, Sara and Collins, {Karl D.} and Hiroshi Matsubara and Malcolm Spain and Procter, {David J.}",

year = "2009",

month = jun,

day = "3",

doi = "10.1021/ja901715d",

language = "English",

volume = "131",

pages = "7214--7215",

journal = "Journal of the American Chemical Society",

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TY - JOUR

T1 - Selective reductions of cyclic 1,3-diesters using SmI2 and H2O

AU - Guazzelli, Giuditta

AU - De Grazia, Sara

AU - Collins, Karl D.

AU - Matsubara, Hiroshi

AU - Spain, Malcolm

AU - Procter, David J.

PY - 2009/6/3

Y1 - 2009/6/3

N2 - (Chemical Equation Presented) SmI2?H2O reduces cyclic 1,3-diesters to 3-hydroxyacids with no over-reduction. Furthermore, the reagent system is selective for cyclic 1,3-diesters over acyclic 1,3-diesters and esters. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron transfer to the ester carbonyl and the anomeric stabilization of the resulting radical-anion intermediate. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. Copyright © 2009 American Chemical Society.

AB - (Chemical Equation Presented) SmI2?H2O reduces cyclic 1,3-diesters to 3-hydroxyacids with no over-reduction. Furthermore, the reagent system is selective for cyclic 1,3-diesters over acyclic 1,3-diesters and esters. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron transfer to the ester carbonyl and the anomeric stabilization of the resulting radical-anion intermediate. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. Copyright © 2009 American Chemical Society.

U2 - 10.1021/ja901715d

DO - 10.1021/ja901715d

M3 - Article

C2 - 19422232

SN - 0002-7863

VL - 131

SP - 7214

EP - 7215

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 21

ER -

Selective reductions of cyclic 1,3-diesters using SmI2 and H2O

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CCDC 721800: Experimental Crystal Structure Determination

Cite this