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(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

Organocatalysis, now running its second decade of life, is being considered one of the main tools a synthetic chemist has to perform asymmetric catalysis. In this review the synthesis of six-membered rings, that contain multiple chiral centers, either by a ring closing process or by a functionalizat...

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Autores principales: Koutoulogenis, Giorgos, Kaplaneris, Nikolaos, Kokotos, Christoforos G
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4902000/
https://www.ncbi.nlm.nih.gov/pubmed/27340441
http://dx.doi.org/10.3762/bjoc.12.48
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author Koutoulogenis, Giorgos
Kaplaneris, Nikolaos
Kokotos, Christoforos G
author_facet Koutoulogenis, Giorgos
Kaplaneris, Nikolaos
Kokotos, Christoforos G
author_sort Koutoulogenis, Giorgos
collection PubMed
description Organocatalysis, now running its second decade of life, is being considered one of the main tools a synthetic chemist has to perform asymmetric catalysis. In this review the synthesis of six-membered rings, that contain multiple chiral centers, either by a ring closing process or by a functionalization reaction on an already existing six-membered ring, utilizing bifunctional (thio)ureas will be summarized. Initially, the use of primary amine-thioureas as organocatalysts for the above transformation is being discussed, followed by the examples employing secondary amine-thioureas. Finally, the use of tertiary amine-thioureas and miscellaneous examples are presented.
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spelling pubmed-49020002016-06-23 (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers Koutoulogenis, Giorgos Kaplaneris, Nikolaos Kokotos, Christoforos G Beilstein J Org Chem Review Organocatalysis, now running its second decade of life, is being considered one of the main tools a synthetic chemist has to perform asymmetric catalysis. In this review the synthesis of six-membered rings, that contain multiple chiral centers, either by a ring closing process or by a functionalization reaction on an already existing six-membered ring, utilizing bifunctional (thio)ureas will be summarized. Initially, the use of primary amine-thioureas as organocatalysts for the above transformation is being discussed, followed by the examples employing secondary amine-thioureas. Finally, the use of tertiary amine-thioureas and miscellaneous examples are presented. Beilstein-Institut 2016-03-10 /pmc/articles/PMC4902000/ /pubmed/27340441 http://dx.doi.org/10.3762/bjoc.12.48 Text en Copyright © 2016, Koutoulogenis 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 Review
Koutoulogenis, Giorgos
Kaplaneris, Nikolaos
Kokotos, Christoforos G
(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers
title (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers
title_full (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers
title_fullStr (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers
title_full_unstemmed (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers
title_short (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers
title_sort (thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4902000/
https://www.ncbi.nlm.nih.gov/pubmed/27340441
http://dx.doi.org/10.3762/bjoc.12.48
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