(Z)-Selective Takai olefination of salicylaldehydes

The Takai olefination (or Takai reaction) is a method for the conversion of aldehydes to vinyl iodides, and has seen widespread implementation in organic synthesis. The reaction is usually noted for its high (E)-selectivity; however, herein we report the highly (Z)-selective Takai olefination of sal...

Descripción completa

Detalles Bibliográficos
Autores principales: Geddis, Stephen M, Hagerman, Caroline E, Galloway, Warren R J D, Sore, Hannah F, Goodman, Jonathan M, Spring, David R
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5331342/
https://www.ncbi.nlm.nih.gov/pubmed/28326141
http://dx.doi.org/10.3762/bjoc.13.35
_version_ 1782511355584053248
author Geddis, Stephen M
Hagerman, Caroline E
Galloway, Warren R J D
Sore, Hannah F
Goodman, Jonathan M
Spring, David R
author_facet Geddis, Stephen M
Hagerman, Caroline E
Galloway, Warren R J D
Sore, Hannah F
Goodman, Jonathan M
Spring, David R
author_sort Geddis, Stephen M
collection PubMed
description The Takai olefination (or Takai reaction) is a method for the conversion of aldehydes to vinyl iodides, and has seen widespread implementation in organic synthesis. The reaction is usually noted for its high (E)-selectivity; however, herein we report the highly (Z)-selective Takai olefination of salicylaldehyde derivatives. Systematic screening of related substrates led to the identification of key factors responsible for this surprising inversion of selectivity, and enabled the development of a modified mechanistic model to rationalise these observations.
format Online
Article
Text
id pubmed-5331342
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-53313422017-03-21 (Z)-Selective Takai olefination of salicylaldehydes Geddis, Stephen M Hagerman, Caroline E Galloway, Warren R J D Sore, Hannah F Goodman, Jonathan M Spring, David R Beilstein J Org Chem Letter The Takai olefination (or Takai reaction) is a method for the conversion of aldehydes to vinyl iodides, and has seen widespread implementation in organic synthesis. The reaction is usually noted for its high (E)-selectivity; however, herein we report the highly (Z)-selective Takai olefination of salicylaldehyde derivatives. Systematic screening of related substrates led to the identification of key factors responsible for this surprising inversion of selectivity, and enabled the development of a modified mechanistic model to rationalise these observations. Beilstein-Institut 2017-02-20 /pmc/articles/PMC5331342/ /pubmed/28326141 http://dx.doi.org/10.3762/bjoc.13.35 Text en Copyright © 2017, Geddis et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Geddis, Stephen M
Hagerman, Caroline E
Galloway, Warren R J D
Sore, Hannah F
Goodman, Jonathan M
Spring, David R
(Z)-Selective Takai olefination of salicylaldehydes
title (Z)-Selective Takai olefination of salicylaldehydes
title_full (Z)-Selective Takai olefination of salicylaldehydes
title_fullStr (Z)-Selective Takai olefination of salicylaldehydes
title_full_unstemmed (Z)-Selective Takai olefination of salicylaldehydes
title_short (Z)-Selective Takai olefination of salicylaldehydes
title_sort (z)-selective takai olefination of salicylaldehydes
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5331342/
https://www.ncbi.nlm.nih.gov/pubmed/28326141
http://dx.doi.org/10.3762/bjoc.13.35
work_keys_str_mv AT geddisstephenm zselectivetakaiolefinationofsalicylaldehydes
AT hagermancarolinee zselectivetakaiolefinationofsalicylaldehydes
AT gallowaywarrenrjd zselectivetakaiolefinationofsalicylaldehydes
AT sorehannahf zselectivetakaiolefinationofsalicylaldehydes
AT goodmanjonathanm zselectivetakaiolefinationofsalicylaldehydes
AT springdavidr zselectivetakaiolefinationofsalicylaldehydes

Ejemplares similares