AI Article Synopsis
- A new method has been created for the efficient synthesis of natural and non-natural isopavine alkaloids, focusing on enantioselectivity.
- The process utilizes a catalytic asymmetric reaction that achieves a high level of enantioselectivity (95-98% ee) to form a key stereogenic center.
- It also incorporates an intramolecular Pictet-Spengler reaction, allowing for the quick and selective construction of the complex tetracyclic structure.
Article Abstract
A concise, versatile, and catalytic enantioselective approach to natural and non-natural isopavine alkaloids has been developed. The synthesis takes advantage of catalytic asymmetric reaction to construct the pivotal stereogenic center in a highly enantioselective way (95-98% ee), and features use of intramolecular Pictet-Spengler reaction to build the core tetracyclic skeleton in a rapid and stereoselective fashion.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.7b02385 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Copper-catalyzed intermolecular Regio- and Enantioselective Hydrosilylation of Alkenes with Prochiral Silanes.
Nat Commun
January 2025
Department of Chemistry, University of Science and Technology of China, Hefei, PR China.
This study presents a copper-catalyzed, substrate-controlled regio- and enantioselective intermolecular hydrosilylation method capable of accommodating a broad scope of alkenes and prochiral silanes. The approach offers an efficient and versatile pathway to generate enantioenriched linear and branched alkyl-substituted Si-stereogenic silanes. Key features of this reaction include mild reaction conditions, simple catalytic systems, compatibility with diverse substrates, high yields and enantioselectivities.
View Article and Find Full Text PDFChiral synthetic hosts for efficient enantioselective molecular recognition. Design principles and synthetic aspects.
Chem Commun (Camb)
January 2025
Institut de Química Computacional i Catàlisi (IQCC), Universitat de Girona, Maria Aurèlia Capmany 69, 17003 Girona, Spain.
Discrimination of enantiomeric substrate molecules is one of the fundamental properties of biological hosts. Replicating enantioselective molecular recognition with synthetic receptors is a topic of interest with implications in diverse applications such as bioinspired enantioselective catalysis, enantiomer separation, or sensing. In this review, five different systems reported in the literature are discussed, and their performance and versatility are analyzed.
View Article and Find Full Text PDFPhotoinduced Regiodivergent and Enantioselective Cross-Coupling of Glycine Derivatives with Hydrocarbon Feedstocks.
J Am Chem Soc
January 2025
Key Laboratory of Chemical Biology of Fujian Province, iChEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
Regiodivergent asymmetric synthesis represents a transformative strategy for the efficient generation of structurally diverse chiral products from a single set of starting materials, significantly enriching their enantiomeric composition. However, the design of radical-mediated regiodivergent and enantioselective reactions that can accommodate a wide range of functional groups and substrates has posed significant challenges. The obstacles primarily lie in switching the regioselectivity and achieving high enantiodiscrimination, especially when dealing with high-energy intermediates.
View Article and Find Full Text PDFOn the gold(I)-catalyzed enantioselective addition of indole to diphenylallene via anion-binding catalysis.
Tetrahedron Lett
October 2024
Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Neutral dual hydrogen bond donors (HBDs) are effective catalysts that enhance the electrophilicity of substrates or the Lewis/Brønsted acidity of reagents through an anion-binding mechanism. Despite their success in various enantioselective organocatalytic reactions, their application to transition metal catalysis remains rare. Herein, we report the activation of gold(I) precatalysts by chiral ureas, leading to enantioselective hydroarylation of allenes with indoles.
View Article and Find Full Text PDFReticulating Crystalline Porous Materials for Asymmetric Heterogeneous Catalysis.
Adv Mater
December 2024
School of Chemistry and Chemical Engineering and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai, 200240, China.
Asymmetric catalysis is essential for addressing the increasing demand for enantiopure compounds. Recent advances in reticular chemistry have demonstrated that metal-organic frameworks (MOFs) and covalent organic frameworks (COFs) possess highly regular porous architectures, exceptional tunability, and the ability to incorporate chiral functionalities through their open channels or cavities. These characteristics make them highly effective and enantioselective catalysts for a wide range of asymmetric transformations.
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!