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Intercepting the Gold‐Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols
The regioselective gold‐catalysed hydration of propargylic alcohols to β‐hydroxy ketones can be achieved by diverting the gold‐catalysed Meyer–Schuster rearrangement through the addition of a protic additive with a pK (a) of 7–9 such as p‐nitrophenol, boric acid or a boronic acid. This provides an i...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5698882/ https://www.ncbi.nlm.nih.gov/pubmed/29200990 http://dx.doi.org/10.1002/adsc.201600101 |
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author | Pennell, Matthew N. Kyle, Michael P. Gibson, Samantha M. Male, Louise Turner, Peter G. Grainger, Richard S. Sheppard, Tom D. |
author_facet | Pennell, Matthew N. Kyle, Michael P. Gibson, Samantha M. Male, Louise Turner, Peter G. Grainger, Richard S. Sheppard, Tom D. |
author_sort | Pennell, Matthew N. |
collection | PubMed |
description | The regioselective gold‐catalysed hydration of propargylic alcohols to β‐hydroxy ketones can be achieved by diverting the gold‐catalysed Meyer–Schuster rearrangement through the addition of a protic additive with a pK (a) of 7–9 such as p‐nitrophenol, boric acid or a boronic acid. This provides an interesting alternative to an aldol reaction when combined with the straightforward addition of an alkyne to an aldehyde or ketone. The gold‐catalysed reaction of an electron‐deficient, sterically hindered propargylic alcohol with a boronic acid led to the formation of an unusually stable cyclic boron enolate. [Image: see text] |
format | Online Article Text |
id | pubmed-5698882 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-56988822017-11-30 Intercepting the Gold‐Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols Pennell, Matthew N. Kyle, Michael P. Gibson, Samantha M. Male, Louise Turner, Peter G. Grainger, Richard S. Sheppard, Tom D. Adv Synth Catal Updates The regioselective gold‐catalysed hydration of propargylic alcohols to β‐hydroxy ketones can be achieved by diverting the gold‐catalysed Meyer–Schuster rearrangement through the addition of a protic additive with a pK (a) of 7–9 such as p‐nitrophenol, boric acid or a boronic acid. This provides an interesting alternative to an aldol reaction when combined with the straightforward addition of an alkyne to an aldehyde or ketone. The gold‐catalysed reaction of an electron‐deficient, sterically hindered propargylic alcohol with a boronic acid led to the formation of an unusually stable cyclic boron enolate. [Image: see text] John Wiley and Sons Inc. 2016-04-27 2016-04-28 /pmc/articles/PMC5698882/ /pubmed/29200990 http://dx.doi.org/10.1002/adsc.201600101 Text en © 2016. The Author. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Updates Pennell, Matthew N. Kyle, Michael P. Gibson, Samantha M. Male, Louise Turner, Peter G. Grainger, Richard S. Sheppard, Tom D. Intercepting the Gold‐Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols |
title | Intercepting the Gold‐Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols |
title_full | Intercepting the Gold‐Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols |
title_fullStr | Intercepting the Gold‐Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols |
title_full_unstemmed | Intercepting the Gold‐Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols |
title_short | Intercepting the Gold‐Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols |
title_sort | intercepting the gold‐catalysed meyer–schuster rearrangement by controlled protodemetallation: a regioselective hydration of propargylic alcohols |
topic | Updates |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5698882/ https://www.ncbi.nlm.nih.gov/pubmed/29200990 http://dx.doi.org/10.1002/adsc.201600101 |
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