Cargando…

Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts

The organocatalysis-based dynamic kinetic resolution (DKR) process has proved to be a powerful strategy for the construction of chiral compounds. In this feature review, we summarized recent progress on the DKR process, which was promoted by chiral bifunctional (thio)urea and squaramide catalysis vi...

Descripción completa

Detalles Bibliográficos
Autores principales: Li, Pan, Hu, Xinquan, Dong, Xiu-Qin, Zhang, Xumu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273922/
https://www.ncbi.nlm.nih.gov/pubmed/27754440
http://dx.doi.org/10.3390/molecules21101327
_version_ 1783377498705231872
author Li, Pan
Hu, Xinquan
Dong, Xiu-Qin
Zhang, Xumu
author_facet Li, Pan
Hu, Xinquan
Dong, Xiu-Qin
Zhang, Xumu
author_sort Li, Pan
collection PubMed
description The organocatalysis-based dynamic kinetic resolution (DKR) process has proved to be a powerful strategy for the construction of chiral compounds. In this feature review, we summarized recent progress on the DKR process, which was promoted by chiral bifunctional (thio)urea and squaramide catalysis via hydrogen-bonding interactions between substrates and catalysts. A wide range of asymmetric reactions involving DKR, such as asymmetric alcoholysis of azlactones, asymmetric Michael–Michael cascade reaction, and enantioselective selenocyclization, are reviewed and demonstrate the efficiency of this strategy. The (thio)urea and squaramide catalysts with dual activation would be efficient for more unmet challenges in dynamic kinetic resolution.
format Online
Article
Text
id pubmed-6273922
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62739222018-12-28 Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts Li, Pan Hu, Xinquan Dong, Xiu-Qin Zhang, Xumu Molecules Review The organocatalysis-based dynamic kinetic resolution (DKR) process has proved to be a powerful strategy for the construction of chiral compounds. In this feature review, we summarized recent progress on the DKR process, which was promoted by chiral bifunctional (thio)urea and squaramide catalysis via hydrogen-bonding interactions between substrates and catalysts. A wide range of asymmetric reactions involving DKR, such as asymmetric alcoholysis of azlactones, asymmetric Michael–Michael cascade reaction, and enantioselective selenocyclization, are reviewed and demonstrate the efficiency of this strategy. The (thio)urea and squaramide catalysts with dual activation would be efficient for more unmet challenges in dynamic kinetic resolution. MDPI 2016-10-14 /pmc/articles/PMC6273922/ /pubmed/27754440 http://dx.doi.org/10.3390/molecules21101327 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Li, Pan
Hu, Xinquan
Dong, Xiu-Qin
Zhang, Xumu
Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts
title Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts
title_full Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts
title_fullStr Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts
title_full_unstemmed Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts
title_short Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts
title_sort recent advances in dynamic kinetic resolution by chiral bifunctional (thio)urea- and squaramide-based organocatalysts
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273922/
https://www.ncbi.nlm.nih.gov/pubmed/27754440
http://dx.doi.org/10.3390/molecules21101327
work_keys_str_mv AT lipan recentadvancesindynamickineticresolutionbychiralbifunctionalthioureaandsquaramidebasedorganocatalysts
AT huxinquan recentadvancesindynamickineticresolutionbychiralbifunctionalthioureaandsquaramidebasedorganocatalysts
AT dongxiuqin recentadvancesindynamickineticresolutionbychiralbifunctionalthioureaandsquaramidebasedorganocatalysts
AT zhangxumu recentadvancesindynamickineticresolutionbychiralbifunctionalthioureaandsquaramidebasedorganocatalysts