Solvent-Dependent Divergent Functions of Sc(OTf)(3) in Stereoselective Epoxide-Opening Spiroketalizations

[Image: see text] A stereocontrolled synthesis of benzannulated spiroketals has been developed using solvent-dependent Sc(OTf)(3)-mediated spirocyclizations of exo-glycal epoxides having alcohol side chains. In THF, the reaction proceeds via Lewis acid catalysis under kinetic control with inversion...

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Autores principales: Sharma, Indrajeet, Wurst, Jacqueline M., Tan, Derek S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018158/
https://www.ncbi.nlm.nih.gov/pubmed/24742081
http://dx.doi.org/10.1021/ol500853q
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author Sharma, Indrajeet
Wurst, Jacqueline M.
Tan, Derek S.
author_facet Sharma, Indrajeet
Wurst, Jacqueline M.
Tan, Derek S.
author_sort Sharma, Indrajeet
collection PubMed
description [Image: see text] A stereocontrolled synthesis of benzannulated spiroketals has been developed using solvent-dependent Sc(OTf)(3)-mediated spirocyclizations of exo-glycal epoxides having alcohol side chains. In THF, the reaction proceeds via Lewis acid catalysis under kinetic control with inversion of configuration at the anomeric carbon. In contrast, in CH(2)Cl(2), Brønsted acid catalysis under thermodynamic control leads to retention of configuration. The reactions accommodate a variety of aryl substituents and ring sizes and provide stereochemically diverse spiroketals.
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spelling pubmed-40181582015-04-17 Solvent-Dependent Divergent Functions of Sc(OTf)(3) in Stereoselective Epoxide-Opening Spiroketalizations Sharma, Indrajeet Wurst, Jacqueline M. Tan, Derek S. Org Lett [Image: see text] A stereocontrolled synthesis of benzannulated spiroketals has been developed using solvent-dependent Sc(OTf)(3)-mediated spirocyclizations of exo-glycal epoxides having alcohol side chains. In THF, the reaction proceeds via Lewis acid catalysis under kinetic control with inversion of configuration at the anomeric carbon. In contrast, in CH(2)Cl(2), Brønsted acid catalysis under thermodynamic control leads to retention of configuration. The reactions accommodate a variety of aryl substituents and ring sizes and provide stereochemically diverse spiroketals. American Chemical Society 2014-04-17 2014-05-02 /pmc/articles/PMC4018158/ /pubmed/24742081 http://dx.doi.org/10.1021/ol500853q Text en Copyright © 2014 American Chemical Society
spellingShingle Sharma, Indrajeet
Wurst, Jacqueline M.
Tan, Derek S.
Solvent-Dependent Divergent Functions of Sc(OTf)(3) in Stereoselective Epoxide-Opening Spiroketalizations
title Solvent-Dependent Divergent Functions of Sc(OTf)(3) in Stereoselective Epoxide-Opening Spiroketalizations
title_full Solvent-Dependent Divergent Functions of Sc(OTf)(3) in Stereoselective Epoxide-Opening Spiroketalizations
title_fullStr Solvent-Dependent Divergent Functions of Sc(OTf)(3) in Stereoselective Epoxide-Opening Spiroketalizations
title_full_unstemmed Solvent-Dependent Divergent Functions of Sc(OTf)(3) in Stereoselective Epoxide-Opening Spiroketalizations
title_short Solvent-Dependent Divergent Functions of Sc(OTf)(3) in Stereoselective Epoxide-Opening Spiroketalizations
title_sort solvent-dependent divergent functions of sc(otf)(3) in stereoselective epoxide-opening spiroketalizations
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018158/
https://www.ncbi.nlm.nih.gov/pubmed/24742081
http://dx.doi.org/10.1021/ol500853q
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AT wurstjacquelinem solventdependentdivergentfunctionsofscotf3instereoselectiveepoxideopeningspiroketalizations
AT tandereks solventdependentdivergentfunctionsofscotf3instereoselectiveepoxideopeningspiroketalizations

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