Ephedrine-derived sulfamide-amine alcohol 3 was found to be an effective catalyst for the asymmetric phenylacetylene addition to aldehydes at room temperature without using Ti(O(i)Pr)4 and Zn(OTf)2. It afforded the propargylic alcohols in high yields (up to 99%) and good enantioselectivities (up to 84% ee), which were much higher than that based on N-methylephedrine under the same reaction conditions. Its weakly coordinative sulfonamide moiety of the ligand plays an important role for further acceleration and stereocontrol in the alkynylation.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chir.20165 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Fe-Doped 4-Aminophenylacetylene-Derived Red Emissive Polymer Carbon Dots: Synthesis and Anti-Counterfeiting Applications.
ACS Appl Mater Interfaces
January 2025
National Joint Engineering Research Center for Highly-Efficient Utilization Technology of Forestry Resource, Southwest Forestry University, Kunming 650224, P. R. China.
Phenylacetylene derivatives serve as typical monomers for polyaddition reactions. In this study, we present a straightforward one-step protocol for synthesizing polyacetylene P0 (undoped), P0.09 (doped with 0.
View Article and Find Full Text PDFAn Acceptor-Substituted -Heterocyclic -Quinodimethane: Pushing the Boundaries of Polarization in Donor-Acceptor-Substituted Polyenes.
J Am Chem Soc
November 2024
Institut für Organische Chemie, Justus-Liebig-Universität Gießen, Heinrich-Buff-Ring 17, 35392 Gießen, Germany.
We report the synthesis, isolation, and characterization of a stable donor-acceptor substituted -quinodimethane (QDM). This system with an imidazolidine scaffold as the donor can also be referred to as acceptor-substituted --heterocyclic quinodimethane (NHQ). We have examined the extent of polarization of the conjugated π-system using single-crystal X-ray diffraction, NMR and UV/vis spectroscopy, cyclic voltammetry, and DFT computations.
View Article and Find Full Text PDFReactions of a geminal Sc/P Lewis pair with pyridotetrazole and beyond.
Dalton Trans
December 2024
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.
Frustrated Lewis pair (FLP) chemistry has undergone remarkable growth, among which rare-earth metal-based Lewis pairs have exhibited unique reactivity in recent years. Herein, treatment of the intramolecular Sc/P Lewis pair, , (ArO)ScN(Bu)PPh (1, Ar = 2,6-Bu-CH), with pyridotetrazole resulted in the formation of an FLP nitrene adduct with N elimination, offering additional insights into the mechanism of transition-metal-catalyzed denitrogenative annulation of pyridotetrazole. Reactions of complex 1 with 1,3,5-triazine and benzo[]cinnoline generated FLP-type products Sc/P 1,2-addition to the CN bond and the NN bond, respectively.
View Article and Find Full Text PDFA Robust Synthesis of CoP and NiP Nanocatalysts from Hexaethylaminophosphine and Phosphine-Enhanced Phenylacetylene Hydrogenation.
Inorg Chem
September 2024
Laboratoire de Chimie de la Matière Condensée de Paris (LCMCP), Sorbonne Université, CNRS, 4 place Jussieu, Paris 75005, France.
Metal-rich phases of general formula MP have demonstrated interesting catalytic activity, e.g., for hydrogen evolution reaction and for hydrogenations in colloidal suspension.
View Article and Find Full Text PDFAtomically precise alkynyl-protected AgCu nanoclusters: synthesis, structure analysis, and electrocatalytic CO reduction application.
Nanoscale
September 2024
New Energy Research Institute, School of Environment and Energy, South China University of Technology, Guangzhou Higher Education Mega Center, Guangzhou, 510006, China.
Article Synopsis
- Researchers synthesized and analyzed the structure of AgCu(CCAr)(PPh)Cl nanoclusters, which are composed of silver and copper and show unique absorbance features and superatomic properties.
- Using single-crystal X-ray diffraction, they found that AgCu has an icosahedral metal core connected to tetrahedra, leading to impressive electrocatalytic performance in CO reduction, showing 95.26% efficiency and 257.2 mA cm at -1.3 V.
- The study revealed that the high selectivity for CO stems from the removal of a ligand on the Ag atom, showcasing the benefits of using precise metal nanoclusters to explore the structure-performance relationships in catalysis.
Want 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!