Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

Michael addition reactions of triketopiperazine (TKP) derivatives to enones, mediated by a cinchona alkaloid-derived catalyst, deliver products in high yield and enantiomeric ratio (er). Use of unsaturated ester, nitrile or sulfone partners gives bridged hydroxy-diketopiperazine (DKP) products resul...

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Detalles Bibliográficos
Autores principales: Cabanillas, Alejandro, Davies, Christopher D., Male, Louise, Simpkins, Nigel S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5811140/
https://www.ncbi.nlm.nih.gov/pubmed/29560222
http://dx.doi.org/10.1039/c4sc03218g
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author Cabanillas, Alejandro
Davies, Christopher D.
Male, Louise
Simpkins, Nigel S.
author_facet Cabanillas, Alejandro
Davies, Christopher D.
Male, Louise
Simpkins, Nigel S.
author_sort Cabanillas, Alejandro
collection PubMed
description Michael addition reactions of triketopiperazine (TKP) derivatives to enones, mediated by a cinchona alkaloid-derived catalyst, deliver products in high yield and enantiomeric ratio (er). Use of unsaturated ester, nitrile or sulfone partners gives bridged hydroxy-diketopiperazine (DKP) products resulting from a novel Michael addition–ring closure.
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spelling pubmed-58111402018-03-20 Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions Cabanillas, Alejandro Davies, Christopher D. Male, Louise Simpkins, Nigel S. Chem Sci Chemistry Michael addition reactions of triketopiperazine (TKP) derivatives to enones, mediated by a cinchona alkaloid-derived catalyst, deliver products in high yield and enantiomeric ratio (er). Use of unsaturated ester, nitrile or sulfone partners gives bridged hydroxy-diketopiperazine (DKP) products resulting from a novel Michael addition–ring closure. Royal Society of Chemistry 2015-02-01 2014-11-28 /pmc/articles/PMC5811140/ /pubmed/29560222 http://dx.doi.org/10.1039/c4sc03218g Text en This journal is © The Royal Society of Chemistry 2015 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Cabanillas, Alejandro
Davies, Christopher D.
Male, Louise
Simpkins, Nigel S.
Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions
title Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions
title_full Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions
title_fullStr Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions
title_full_unstemmed Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions
title_short Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions
title_sort highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed michael additions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5811140/
https://www.ncbi.nlm.nih.gov/pubmed/29560222
http://dx.doi.org/10.1039/c4sc03218g
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AT malelouise highlyenantioselectiveaccesstodiketopiperazinesviacinchonaalkaloidcatalyzedmichaeladditions
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