Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity

A new guanidine-thiourea organocatalyst has been developed and applied as bifunctional organocatalyst in the Michael addition reaction of diethyl malonate to trans-β-nitrostyrene. Extensive DFT calculations, including solvent effects and dispersion corrections, as well as ab initio calculations prov...

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Autores principales: Shubina, Tatyana E, Freund, Matthias, Schenker, Sebastian, Clark, Timothy, Tsogoeva, Svetlana B
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/PMC3458773/
https://www.ncbi.nlm.nih.gov/pubmed/23019483
http://dx.doi.org/10.3762/bjoc.8.168
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author Shubina, Tatyana E
Freund, Matthias
Schenker, Sebastian
Clark, Timothy
Tsogoeva, Svetlana B
author_facet Shubina, Tatyana E
Freund, Matthias
Schenker, Sebastian
Clark, Timothy
Tsogoeva, Svetlana B
author_sort Shubina, Tatyana E
collection PubMed
description A new guanidine-thiourea organocatalyst has been developed and applied as bifunctional organocatalyst in the Michael addition reaction of diethyl malonate to trans-β-nitrostyrene. Extensive DFT calculations, including solvent effects and dispersion corrections, as well as ab initio calculations provide a plausible description of the reaction mechanism.
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spelling pubmed-34587732012-09-27 Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity Shubina, Tatyana E Freund, Matthias Schenker, Sebastian Clark, Timothy Tsogoeva, Svetlana B Beilstein J Org Chem Full Research Paper A new guanidine-thiourea organocatalyst has been developed and applied as bifunctional organocatalyst in the Michael addition reaction of diethyl malonate to trans-β-nitrostyrene. Extensive DFT calculations, including solvent effects and dispersion corrections, as well as ab initio calculations provide a plausible description of the reaction mechanism. Beilstein-Institut 2012-09-07 /pmc/articles/PMC3458773/ /pubmed/23019483 http://dx.doi.org/10.3762/bjoc.8.168 Text en Copyright © 2012, Shubina 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
Shubina, Tatyana E
Freund, Matthias
Schenker, Sebastian
Clark, Timothy
Tsogoeva, Svetlana B
Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity
title Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity
title_full Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity
title_fullStr Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity
title_full_unstemmed Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity
title_short Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity
title_sort synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-michael reaction: theoretical studies on mechanism and enantioselectivity
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458773/
https://www.ncbi.nlm.nih.gov/pubmed/23019483
http://dx.doi.org/10.3762/bjoc.8.168
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