Chirality Transfer in Gold(I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes

Gold(I)‐catalysed intermolecular hydroalkoxylation of enantioenriched 1,3‐disubstituted allenes was previously reported to occur with poor chirality transfer due to rapid allene racemisation. The first intermolecular hydroalkoxylation of allenes with efficient chirality transfer is reported here, ex...

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Detalles Bibliográficos
Autores principales: Webster, Stacey, Sutherland, Daniel R., Lee, Ai‐Lan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5215423/
https://www.ncbi.nlm.nih.gov/pubmed/27862422
http://dx.doi.org/10.1002/chem.201603918
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author Webster, Stacey
Sutherland, Daniel R.
Lee, Ai‐Lan
author_facet Webster, Stacey
Sutherland, Daniel R.
Lee, Ai‐Lan
author_sort Webster, Stacey
collection PubMed
description Gold(I)‐catalysed intermolecular hydroalkoxylation of enantioenriched 1,3‐disubstituted allenes was previously reported to occur with poor chirality transfer due to rapid allene racemisation. The first intermolecular hydroalkoxylation of allenes with efficient chirality transfer is reported here, exploiting conditions that suppress allene racemisation. A full substrate scope study reveals that excellent regio‐ and stereoselectivities are achieved when a σ‐withdrawing substituent is present.
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spelling pubmed-52154232017-01-18 Chirality Transfer in Gold(I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes Webster, Stacey Sutherland, Daniel R. Lee, Ai‐Lan Chemistry Full Papers Gold(I)‐catalysed intermolecular hydroalkoxylation of enantioenriched 1,3‐disubstituted allenes was previously reported to occur with poor chirality transfer due to rapid allene racemisation. The first intermolecular hydroalkoxylation of allenes with efficient chirality transfer is reported here, exploiting conditions that suppress allene racemisation. A full substrate scope study reveals that excellent regio‐ and stereoselectivities are achieved when a σ‐withdrawing substituent is present. John Wiley and Sons Inc. 2016-11-11 2016-12-19 /pmc/articles/PMC5215423/ /pubmed/27862422 http://dx.doi.org/10.1002/chem.201603918 Text en © 2016 The Authors. 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 Full Papers
Webster, Stacey
Sutherland, Daniel R.
Lee, Ai‐Lan
Chirality Transfer in Gold(I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes
title Chirality Transfer in Gold(I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes
title_full Chirality Transfer in Gold(I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes
title_fullStr Chirality Transfer in Gold(I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes
title_full_unstemmed Chirality Transfer in Gold(I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes
title_short Chirality Transfer in Gold(I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes
title_sort chirality transfer in gold(i)‐catalysed hydroalkoxylation of 1,3‐disubstituted allenes
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5215423/
https://www.ncbi.nlm.nih.gov/pubmed/27862422
http://dx.doi.org/10.1002/chem.201603918
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AT leeailan chiralitytransferingoldicatalysedhydroalkoxylationof13disubstitutedallenes

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