Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes

ABSTRACT: Ru-catalyzed synthesis of mixed alkyl–alkyl acetals via addition of primary alcohols to allyl ethers has been extended to include long-chain and/or functionalized substrates. The catalytic systems for these reactions were generated from RuCl(2)(PPh(3))(3) and [RuCl(2)(1,5-COD)](x) and phos...

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Autores principales: Krompiec, Stanisław, Penkala, Mateusz, Kowalska, Ewelina, Penczek, Robert, Bujak, Piotr, Danikiewicz, Witold, Spólnik, Grzegorz, Kita, Andrzej, Grudzka, Iwona
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2011
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4495020/
https://www.ncbi.nlm.nih.gov/pubmed/26166855
http://dx.doi.org/10.1007/s00706-011-0638-8
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author Krompiec, Stanisław
Penkala, Mateusz
Kowalska, Ewelina
Penczek, Robert
Bujak, Piotr
Danikiewicz, Witold
Spólnik, Grzegorz
Kita, Andrzej
Grudzka, Iwona
author_facet Krompiec, Stanisław
Penkala, Mateusz
Kowalska, Ewelina
Penczek, Robert
Bujak, Piotr
Danikiewicz, Witold
Spólnik, Grzegorz
Kita, Andrzej
Grudzka, Iwona
author_sort Krompiec, Stanisław
collection PubMed
description ABSTRACT: Ru-catalyzed synthesis of mixed alkyl–alkyl acetals via addition of primary alcohols to allyl ethers has been extended to include long-chain and/or functionalized substrates. The catalytic systems for these reactions were generated from RuCl(2)(PPh(3))(3) and [RuCl(2)(1,5-COD)](x) and phosphines [PPh(3) or P(p-chlorophenyl)(3)] or SbPh(3). Of particular importance is the almost quantitative elimination of transacetalization. The addition proceeds through allyl complexes, not via isomerization of allyl ethers––subsequent addition of ROH to vinyl ethers. GRAPHICAL ABSTRACT: [Image: see text]
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spelling pubmed-44950202015-07-09 Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes Krompiec, Stanisław Penkala, Mateusz Kowalska, Ewelina Penczek, Robert Bujak, Piotr Danikiewicz, Witold Spólnik, Grzegorz Kita, Andrzej Grudzka, Iwona Monatsh Chem Original Paper ABSTRACT: Ru-catalyzed synthesis of mixed alkyl–alkyl acetals via addition of primary alcohols to allyl ethers has been extended to include long-chain and/or functionalized substrates. The catalytic systems for these reactions were generated from RuCl(2)(PPh(3))(3) and [RuCl(2)(1,5-COD)](x) and phosphines [PPh(3) or P(p-chlorophenyl)(3)] or SbPh(3). Of particular importance is the almost quantitative elimination of transacetalization. The addition proceeds through allyl complexes, not via isomerization of allyl ethers––subsequent addition of ROH to vinyl ethers. GRAPHICAL ABSTRACT: [Image: see text] Springer Vienna 2011-10-27 2011 /pmc/articles/PMC4495020/ /pubmed/26166855 http://dx.doi.org/10.1007/s00706-011-0638-8 Text en © The Author(s) 2011 https://creativecommons.org/licenses/by-nc/4.0/ This article is distributed under the terms of the Creative Commons Attribution Noncommercial License which permits any noncommercial use, distribution, and reproduction in any medium, provided the original author(s) and source are credited.
spellingShingle Original Paper
Krompiec, Stanisław
Penkala, Mateusz
Kowalska, Ewelina
Penczek, Robert
Bujak, Piotr
Danikiewicz, Witold
Spólnik, Grzegorz
Kita, Andrzej
Grudzka, Iwona
Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes
title Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes
title_full Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes
title_fullStr Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes
title_full_unstemmed Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes
title_short Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes
title_sort synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4495020/
https://www.ncbi.nlm.nih.gov/pubmed/26166855
http://dx.doi.org/10.1007/s00706-011-0638-8
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