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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Main Authors:	Tatyana E. Shubina, Matthias Freund, Sebastian Schenker, Timothy Clark, Svetlana B. Tsogoeva
Format:	Article
Language:	English
Published:	Beilstein-Institut 2012-09-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	bifunctional organocatalyst DFT calculations guanidine-thiourea Michael addition organocatalysis transition states
Online Access:	https://doi.org/10.3762/bjoc.8.168

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spelling	doaj-409040093eff4b0484b10b908c4d49112021-03-02T11:05:07ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-09-01811485149810.3762/bjoc.8.1681860-5397-8-168Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivityTatyana E. Shubina0Matthias Freund1Sebastian Schenker2Timothy Clark3Svetlana B. Tsogoeva4Computer Chemistry Center and Interdisciplinary Center for Molecular Materials, University of Erlangen-Nuremberg, Nägelsbachstr. 25, 91052 Erlangen, GermanyDepartment of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nuremberg, Henkestraße 42, 91054, Erlangen, GermanyDepartment of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nuremberg, Henkestraße 42, 91054, Erlangen, GermanyComputer Chemistry Center and Interdisciplinary Center for Molecular Materials, University of Erlangen-Nuremberg, Nägelsbachstr. 25, 91052 Erlangen, GermanyDepartment of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nuremberg, Henkestraße 42, 91054, Erlangen, GermanyA 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.https://doi.org/10.3762/bjoc.8.168bifunctional organocatalystDFT calculationsguanidine-thioureaMichael additionorganocatalysistransition states
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Tatyana E. Shubina Matthias Freund Sebastian Schenker Timothy Clark Svetlana B. Tsogoeva
spellingShingle	Tatyana E. Shubina Matthias Freund Sebastian Schenker Timothy Clark Svetlana B. Tsogoeva Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity Beilstein Journal of Organic Chemistry bifunctional organocatalyst DFT calculations guanidine-thiourea Michael addition organocatalysis transition states
author_facet	Tatyana E. Shubina Matthias Freund Sebastian Schenker Timothy Clark Svetlana B. Tsogoeva
author_sort	Tatyana E. Shubina
title	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_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_sort	synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-michael reaction: theoretical studies on mechanism and enantioselectivity
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2012-09-01
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.
topic	bifunctional organocatalyst DFT calculations guanidine-thiourea Michael addition organocatalysis transition states
url	https://doi.org/10.3762/bjoc.8.168
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_version_	1724235425189462016

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

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