A multicomponent approach for the preparation of homoallylic alcohols

Here we report the in situ generation of transient allylic boronic species, by reacting TMSCHN(2) and E-vinyl boronic acids, followed by their subsequent trapping with aldehydes as electrophiles to yield homoallylic alcohols. This metal-free reaction was initially discovered by the use of a flow che...

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Detalles Bibliográficos
Autores principales: Poh, Jian-Siang, Lau, Shing-Hing, Dykes, Iain G., Tran, Duc N., Battilocchio, Claudio, Ley, Steven V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5134730/
https://www.ncbi.nlm.nih.gov/pubmed/28042466
http://dx.doi.org/10.1039/c6sc02581a
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author Poh, Jian-Siang
Lau, Shing-Hing
Dykes, Iain G.
Tran, Duc N.
Battilocchio, Claudio
Ley, Steven V.
author_facet Poh, Jian-Siang
Lau, Shing-Hing
Dykes, Iain G.
Tran, Duc N.
Battilocchio, Claudio
Ley, Steven V.
author_sort Poh, Jian-Siang
collection PubMed
description Here we report the in situ generation of transient allylic boronic species, by reacting TMSCHN(2) and E-vinyl boronic acids, followed by their subsequent trapping with aldehydes as electrophiles to yield homoallylic alcohols. This metal-free reaction was initially discovered by the use of a flow chemistry approach to generate a variety of homoallylic alcohols in a straightforward fashion and then transferred to a batch protocol.
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spelling pubmed-51347302016-12-30 A multicomponent approach for the preparation of homoallylic alcohols Poh, Jian-Siang Lau, Shing-Hing Dykes, Iain G. Tran, Duc N. Battilocchio, Claudio Ley, Steven V. Chem Sci Chemistry Here we report the in situ generation of transient allylic boronic species, by reacting TMSCHN(2) and E-vinyl boronic acids, followed by their subsequent trapping with aldehydes as electrophiles to yield homoallylic alcohols. This metal-free reaction was initially discovered by the use of a flow chemistry approach to generate a variety of homoallylic alcohols in a straightforward fashion and then transferred to a batch protocol. Royal Society of Chemistry 2016-11-01 2016-07-08 /pmc/articles/PMC5134730/ /pubmed/28042466 http://dx.doi.org/10.1039/c6sc02581a Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Poh, Jian-Siang
Lau, Shing-Hing
Dykes, Iain G.
Tran, Duc N.
Battilocchio, Claudio
Ley, Steven V.
A multicomponent approach for the preparation of homoallylic alcohols
title A multicomponent approach for the preparation of homoallylic alcohols
title_full A multicomponent approach for the preparation of homoallylic alcohols
title_fullStr A multicomponent approach for the preparation of homoallylic alcohols
title_full_unstemmed A multicomponent approach for the preparation of homoallylic alcohols
title_short A multicomponent approach for the preparation of homoallylic alcohols
title_sort multicomponent approach for the preparation of homoallylic alcohols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5134730/
https://www.ncbi.nlm.nih.gov/pubmed/28042466
http://dx.doi.org/10.1039/c6sc02581a
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