A series of γ-hydroxy amides were synthesized with high enantioselectivities (up to 99%) using asymmetric hydrogenation of the corresponding γ-ketoamides in the presence of Ru-Xyl-SunPhos-Daipen catalyst providing key building blocks for a variety of naturally occurring and biologically active compounds.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo5008916 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Leveraging the Stereochemical Complexity of Octahedral Diastereomeric-at-Metal Catalysts to Unlock Regio-, Diastereo-, and Enantioselectivity in Alcohol-Mediated C-C Couplings via Hydrogen Transfer.
J Am Chem Soc
March 2024
Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.
Experimental and computational studies illuminating the factors that guide metal-centered stereogenicity and, therefrom, selectivity in transfer hydrogenative carbonyl additions of alcohol proelectrophiles catalyzed by chiral-at-metal-and-ligand octahedral d metal ions, iridium(III) and ruthenium(II), are described. To augment or invert regio-, diastereo-, and enantioselectivity, predominantly one from among as many as 15 diastereomeric-at-metal complexes is required. For iridium(III) catalysts, cyclometalation assists in defining the metal stereocenter, and for ruthenium(II) catalysts, iodide counterions play a key role.
View Article and Find Full Text PDFChiral Ru-Based Covalent Organic Frameworks as An Electrochemiluminescence-Active Platform for the Enantioselective Sensing of Amino Acids.
ACS Appl Mater Interfaces
March 2024
Jiangsu Key Laboratory of Advanced Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
Although several studies related with the electrochemiluminescence (ECL) technique have been reported for chiral discrimination, it still has to face some limitations, namely, complex synthetic pathways and a relatively low recognition efficiency. Herein, this study introduces a facile strategy for the synthesis of ECL-active chiral covalent organic frameworks (COFs) employed as a chiral recognition platform. In this artificial structure, ruthenium(II) coordinated with the dipyridyl unit of the COF and enantiopure cyclohexane-1,2-diamine was harnessed as the ECL-active unit, which gave strong ECL emission in the presence of the coreactant reagent (KSO).
View Article and Find Full Text PDFChiral-at-Ruthenium Catalysts for Nitrene-Mediated Asymmetric C-H Functionalizations.
Acc Chem Res
May 2023
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein Straße 4, 35043 Marburg, Germany.
ConspectusAsymmetric transition metal catalysis is an indispensable tool used both in academia and industry for forging chiral molecules in an enantioselective fashion. Its advancement relies in large part on the design and discovery of new chiral catalysts. In contrast to conventional endeavors of generating chiral transition metal catalysts from carefully tailored chiral ligands, the development of chiral transition metal catalysts containing solely achiral ligands (chiral-at-metal catalysts) has been neglected.
View Article and Find Full Text PDFEnantioselective C-H Bond Functionalization Involving Arene Ruthenium(II) Catalysis.
Chemistry
February 2023
Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education School of Chemistry, Sun Yat-Sen University, Guangzhou, 510006, P. R. China.
The p-Cymene ruthenium(II) complex is one of the most widely used catalysts in C-H activation. However, enantioselective C-H activation promoted by arene ruthenium(II) complexes has not been realized until recently. The revealed strategies include intramolecular nitrene C-H insertion, the use of chiral transient directing groups, chiral carboxylic acid, relay catalysis, and chiral arene ligands.
View Article and Find Full Text PDFChiral Arene Ligand as Stereocontroller for Asymmetric C-H Activation.
Angew Chem Int Ed Engl
June 2022
Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, School of Chemistry, Sun Yat-Sen University, Guangzhou, 510006, P. R. China.
Development of chiral ligands is the most fundamental task in metal-catalyzed asymmetric synthesis. In the last 60 years, various kinds of ligands have been sophisticatedly developed. However, it remains a long-standing challenge to develop practically useful chiral η -arene ligands, thereby seriously hampering the asymmetric synthesis promoted by arene-metal catalysts.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!