Cargando…

A Giese reaction for electron-rich alkenes

A general method for the hydroalkylation of electron-rich terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of...

Descripción completa

Detalles Bibliográficos
Autores principales: Huang, Qi, Suravarapu, Sankar Rao, Renaud, Philippe
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179299/
https://www.ncbi.nlm.nih.gov/pubmed/34163988
http://dx.doi.org/10.1039/d0sc06341j
_version_ 1783703749019041792
author Huang, Qi
Suravarapu, Sankar Rao
Renaud, Philippe
author_facet Huang, Qi
Suravarapu, Sankar Rao
Renaud, Philippe
author_sort Huang, Qi
collection PubMed
description A general method for the hydroalkylation of electron-rich terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of triethylborane acting as a chain transfer reagent and 4-tert-butylcatechol (TBC) as a source of hydrogen atom. The efficacy of the reaction is best explained by very favorable polar effects supporting the chain process and minimizing undesired polar reactions. The stereoselective hydroalkylation of chiral N-(alk-1-en-1-yl)oxazolidin-2-ones takes place with good to excellent diastereocontrol.
format Online
Article
Text
id pubmed-8179299
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-81792992021-06-22 A Giese reaction for electron-rich alkenes Huang, Qi Suravarapu, Sankar Rao Renaud, Philippe Chem Sci Chemistry A general method for the hydroalkylation of electron-rich terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of triethylborane acting as a chain transfer reagent and 4-tert-butylcatechol (TBC) as a source of hydrogen atom. The efficacy of the reaction is best explained by very favorable polar effects supporting the chain process and minimizing undesired polar reactions. The stereoselective hydroalkylation of chiral N-(alk-1-en-1-yl)oxazolidin-2-ones takes place with good to excellent diastereocontrol. The Royal Society of Chemistry 2020-12-17 /pmc/articles/PMC8179299/ /pubmed/34163988 http://dx.doi.org/10.1039/d0sc06341j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Huang, Qi
Suravarapu, Sankar Rao
Renaud, Philippe
A Giese reaction for electron-rich alkenes
title A Giese reaction for electron-rich alkenes
title_full A Giese reaction for electron-rich alkenes
title_fullStr A Giese reaction for electron-rich alkenes
title_full_unstemmed A Giese reaction for electron-rich alkenes
title_short A Giese reaction for electron-rich alkenes
title_sort giese reaction for electron-rich alkenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179299/
https://www.ncbi.nlm.nih.gov/pubmed/34163988
http://dx.doi.org/10.1039/d0sc06341j
work_keys_str_mv AT huangqi agiesereactionforelectronrichalkenes
AT suravarapusankarrao agiesereactionforelectronrichalkenes
AT renaudphilippe agiesereactionforelectronrichalkenes
AT huangqi giesereactionforelectronrichalkenes
AT suravarapusankarrao giesereactionforelectronrichalkenes
AT renaudphilippe giesereactionforelectronrichalkenes