Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition

Rhenium-catalyzed stereoselective transposition of allylic alcohols is reported. In the presence of 1 mol% of Re(2)O(7), (E)- or (Z)-δ-hydroxymethyl-anti-homoallylic alcohols were converted into the acetals of 2-methyl-1,3-syn-diols with excellent diastereoselectivities. 1,3-syn-Diol acetals can als...

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Autores principales: Liu, Jiaming, Chen, Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10395275/
https://www.ncbi.nlm.nih.gov/pubmed/37538826
http://dx.doi.org/10.1039/d2sc07059f
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author Liu, Jiaming
Chen, Ming
author_facet Liu, Jiaming
Chen, Ming
author_sort Liu, Jiaming
collection PubMed
description Rhenium-catalyzed stereoselective transposition of allylic alcohols is reported. In the presence of 1 mol% of Re(2)O(7), (E)- or (Z)-δ-hydroxymethyl-anti-homoallylic alcohols were converted into the acetals of 2-methyl-1,3-syn-diols with excellent diastereoselectivities. 1,3-syn-Diol acetals can also be synthesized from (E)-δ-hydroxymethyl-syn-homoallylic alcohols.
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spelling pubmed-103952752023-08-03 Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition Liu, Jiaming Chen, Ming Chem Sci Chemistry Rhenium-catalyzed stereoselective transposition of allylic alcohols is reported. In the presence of 1 mol% of Re(2)O(7), (E)- or (Z)-δ-hydroxymethyl-anti-homoallylic alcohols were converted into the acetals of 2-methyl-1,3-syn-diols with excellent diastereoselectivities. 1,3-syn-Diol acetals can also be synthesized from (E)-δ-hydroxymethyl-syn-homoallylic alcohols. The Royal Society of Chemistry 2023-07-06 /pmc/articles/PMC10395275/ /pubmed/37538826 http://dx.doi.org/10.1039/d2sc07059f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Liu, Jiaming
Chen, Ming
Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition
title Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition
title_full Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition
title_fullStr Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition
title_full_unstemmed Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition
title_short Stereoselective syntheses of 2-methyl-1,3-diol acetals via Re-catalyzed [1,3]-allylic alcohol transposition
title_sort stereoselective syntheses of 2-methyl-1,3-diol acetals via re-catalyzed [1,3]-allylic alcohol transposition
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10395275/
https://www.ncbi.nlm.nih.gov/pubmed/37538826
http://dx.doi.org/10.1039/d2sc07059f
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AT chenming stereoselectivesynthesesof2methyl13diolacetalsviarecatalyzed13allylicalcoholtransposition

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