Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates

We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution feature...

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Autores principales: Xu, Jun, Qiu, Xiao-Long, Qing, Feng-Ling
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486488/
https://www.ncbi.nlm.nih.gov/pubmed/18941489
http://dx.doi.org/10.3762/bjoc.4.18
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author Xu, Jun
Qiu, Xiao-Long
Qing, Feng-Ling
author_facet Xu, Jun
Qiu, Xiao-Long
Qing, Feng-Ling
author_sort Xu, Jun
collection PubMed
description We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution features a reversal of regioselectivity caused by fluorine.
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spelling pubmed-24864882008-10-20 Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates Xu, Jun Qiu, Xiao-Long Qing, Feng-Ling Beilstein J Org Chem Full Research Paper We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution features a reversal of regioselectivity caused by fluorine. Beilstein-Institut 2008-05-27 /pmc/articles/PMC2486488/ /pubmed/18941489 http://dx.doi.org/10.3762/bjoc.4.18 Text en Copyright © 2008, Xu et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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
Xu, Jun
Qiu, Xiao-Long
Qing, Feng-Ling
Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_full Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_fullStr Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_full_unstemmed Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_short Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_sort understanding the mechanism of pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486488/
https://www.ncbi.nlm.nih.gov/pubmed/18941489
http://dx.doi.org/10.3762/bjoc.4.18
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AT qiuxiaolong understandingthemechanismofpdcatalyzedallylicsubstitutionofthecyclicdifluorinatedcarbonates
AT qingfengling understandingthemechanismofpdcatalyzedallylicsubstitutionofthecyclicdifluorinatedcarbonates

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