Phenylsilane as an effective desulfinylation reagent

The reduction using phenylsilane in a KOH-catalyzed system was applied successfully to the conversion of sulfinyl-substituted cyclopropylcarboxylates into the corresponding alcohols. The presence of sulfinyl substituents in the α-position to the carboxylate group caused a desulfinylation product for...

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Autores principales: Midura, Wanda H, Rzewnicka, Aneta, Krysiak, Jerzy A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550773/
https://www.ncbi.nlm.nih.gov/pubmed/28845195
http://dx.doi.org/10.3762/bjoc.13.150
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author Midura, Wanda H
Rzewnicka, Aneta
Krysiak, Jerzy A
author_facet Midura, Wanda H
Rzewnicka, Aneta
Krysiak, Jerzy A
author_sort Midura, Wanda H
collection PubMed
description The reduction using phenylsilane in a KOH-catalyzed system was applied successfully to the conversion of sulfinyl-substituted cyclopropylcarboxylates into the corresponding alcohols. The presence of sulfinyl substituents in the α-position to the carboxylate group caused a desulfinylation product formation with full regio- and stereoselectivity, instead of a carbonyl group reduction. Investigations performed on different α-sulfinylcarbonyl compounds revealed that phenylsilane treatment constitutes a regiospecific method for the desulfinylation of a-sulfinylesters; for corresponding ketones the reaction course depends on the character of the carbonyl group.
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spelling pubmed-55507732017-08-25 Phenylsilane as an effective desulfinylation reagent Midura, Wanda H Rzewnicka, Aneta Krysiak, Jerzy A Beilstein J Org Chem Full Research Paper The reduction using phenylsilane in a KOH-catalyzed system was applied successfully to the conversion of sulfinyl-substituted cyclopropylcarboxylates into the corresponding alcohols. The presence of sulfinyl substituents in the α-position to the carboxylate group caused a desulfinylation product formation with full regio- and stereoselectivity, instead of a carbonyl group reduction. Investigations performed on different α-sulfinylcarbonyl compounds revealed that phenylsilane treatment constitutes a regiospecific method for the desulfinylation of a-sulfinylesters; for corresponding ketones the reaction course depends on the character of the carbonyl group. Beilstein-Institut 2017-08-01 /pmc/articles/PMC5550773/ /pubmed/28845195 http://dx.doi.org/10.3762/bjoc.13.150 Text en Copyright © 2017, Midura et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Midura, Wanda H
Rzewnicka, Aneta
Krysiak, Jerzy A
Phenylsilane as an effective desulfinylation reagent
title Phenylsilane as an effective desulfinylation reagent
title_full Phenylsilane as an effective desulfinylation reagent
title_fullStr Phenylsilane as an effective desulfinylation reagent
title_full_unstemmed Phenylsilane as an effective desulfinylation reagent
title_short Phenylsilane as an effective desulfinylation reagent
title_sort phenylsilane as an effective desulfinylation reagent
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550773/
https://www.ncbi.nlm.nih.gov/pubmed/28845195
http://dx.doi.org/10.3762/bjoc.13.150
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