Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres

A sequence of regio- and stereoselective carbometalation followed by oxidation of ynamides leads to stereodefined fully substituted enolates that subsequently react with various functionalized allyl bromide reagents to provide the expected products possessing an enantiomerically pure quaternary carb...

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Autores principales: Nairoukh, Zackaria, Kumar, Gunda G. K. S. Narayana, Minko, Yury, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5358538/
https://www.ncbi.nlm.nih.gov/pubmed/28451210
http://dx.doi.org/10.1039/c6sc03036j
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author Nairoukh, Zackaria
Kumar, Gunda G. K. S. Narayana
Minko, Yury
Marek, Ilan
author_facet Nairoukh, Zackaria
Kumar, Gunda G. K. S. Narayana
Minko, Yury
Marek, Ilan
author_sort Nairoukh, Zackaria
collection PubMed
description A sequence of regio- and stereoselective carbometalation followed by oxidation of ynamides leads to stereodefined fully substituted enolates that subsequently react with various functionalized allyl bromide reagents to provide the expected products possessing an enantiomerically pure quaternary carbon stereocentre in the α-position to the carbonyl group in excellent yields and enantiomeric ratios after cleavage of the oxazolidinone moiety. Three new bonds are formed in a single-pot operation.
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spelling pubmed-53585382017-04-27 Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres Nairoukh, Zackaria Kumar, Gunda G. K. S. Narayana Minko, Yury Marek, Ilan Chem Sci Chemistry A sequence of regio- and stereoselective carbometalation followed by oxidation of ynamides leads to stereodefined fully substituted enolates that subsequently react with various functionalized allyl bromide reagents to provide the expected products possessing an enantiomerically pure quaternary carbon stereocentre in the α-position to the carbonyl group in excellent yields and enantiomeric ratios after cleavage of the oxazolidinone moiety. Three new bonds are formed in a single-pot operation. Royal Society of Chemistry 2017-01-01 2016-09-15 /pmc/articles/PMC5358538/ /pubmed/28451210 http://dx.doi.org/10.1039/c6sc03036j 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
Nairoukh, Zackaria
Kumar, Gunda G. K. S. Narayana
Minko, Yury
Marek, Ilan
Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
title Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
title_full Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
title_fullStr Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
title_full_unstemmed Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
title_short Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
title_sort enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5358538/
https://www.ncbi.nlm.nih.gov/pubmed/28451210
http://dx.doi.org/10.1039/c6sc03036j
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