Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones

The organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C–C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of t...

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Autores principales: Žari, Sergei, Kailas, Tiiu, Kudrjashova, Marina, Öeren, Mario, Järving, Ivar, Tamm, Toomas, Lopp, Margus, Kanger, Tõnis
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458770/
https://www.ncbi.nlm.nih.gov/pubmed/23019480
http://dx.doi.org/10.3762/bjoc.8.165
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author Žari, Sergei
Kailas, Tiiu
Kudrjashova, Marina
Öeren, Mario
Järving, Ivar
Tamm, Toomas
Lopp, Margus
Kanger, Tõnis
author_facet Žari, Sergei
Kailas, Tiiu
Kudrjashova, Marina
Öeren, Mario
Järving, Ivar
Tamm, Toomas
Lopp, Margus
Kanger, Tõnis
author_sort Žari, Sergei
collection PubMed
description The organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C–C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of the product was suggested from comparison of the experimental and calculated VCD spectra of the reaction product 3a.
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spelling pubmed-34587702012-09-27 Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones Žari, Sergei Kailas, Tiiu Kudrjashova, Marina Öeren, Mario Järving, Ivar Tamm, Toomas Lopp, Margus Kanger, Tõnis Beilstein J Org Chem Full Research Paper The organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C–C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of the product was suggested from comparison of the experimental and calculated VCD spectra of the reaction product 3a. Beilstein-Institut 2012-09-04 /pmc/articles/PMC3458770/ /pubmed/23019480 http://dx.doi.org/10.3762/bjoc.8.165 Text en Copyright © 2012, Žari et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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 Full Research Paper
Žari, Sergei
Kailas, Tiiu
Kudrjashova, Marina
Öeren, Mario
Järving, Ivar
Tamm, Toomas
Lopp, Margus
Kanger, Tõnis
Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_full Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_fullStr Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_full_unstemmed Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_short Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_sort organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458770/
https://www.ncbi.nlm.nih.gov/pubmed/23019480
http://dx.doi.org/10.3762/bjoc.8.165
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