A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki-Miyaura coupling. The chiral-bridged biphenyl monophosphine ligand L1 was found to be much more effective in the reaction enantioselection than its counterpart binaphthyl monophosphine ligands.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8ob03048k | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes.
ChemistryOpen
December 2024
MTA TTK Lendület Artificial Transporter Research Group, Institute of Materials and Environmental Chemistry, HUN-REN Research Center for Natural Sciences, H-1117, Budapest, Magyar tudósok krt. 2, Hungary.
Novel tetrahydroisoquinoline and piperidine derivatives were selectively synthesized from substituted indenes or cyclopentenes. The process starts with an oxidative cleavage of the ring olefin bond, which gives reactive diformyl intermediates. By a ring-closing step using chiral (R) or (S) α-methylbenzylamine under a reductive amination protocol facilitated ring formation with ring expansion of the corresponding nitrogen-containing heterocycles.
View Article and Find Full Text PDFTransition metal-catalyzed cascade C-H activation/cyclization with alkynes: an update on sulfur-containing directing groups.
Chem Commun (Camb)
December 2024
Department of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, P. R. China.
In light of the extensive applications of sulfur-containing heterocyclic compounds in drug discovery, agrochemicals, and advanced materials, the construction of complex sulfur-containing molecular scaffolds has flourished in recent years. There is a profound interest in synthetic methods for forming carbon-sulfur bonds. Regarding this, transition metal (TM)-catalyzed C-H bond activation has emerged as a valuable means for the rapid formation of C-S bonds, although it is comparatively less explored than C-N or C-C bonds.
View Article and Find Full Text PDFElectrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized -Heterocycles.
J Org Chem
December 2024
Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563003, P. R. China.
A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols with general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range of internal alkene and terminal alkene substrates could produce RCO- and ArCN-functionalized -heterocycles in moderate to high yields without the requirement for external oxidants and metals. These resulting products can subsequently be hydrolyzed to yield valuable NH- and OH-functionalized tetrahydrofurans and tetrahydropyranes under mild conditions.
View Article and Find Full Text PDFFunctional biosynthetic stereodivergence in a gene cluster via a dihydrosydnone N-oxide.
Commun Chem
December 2024
Department of Chemistry, University of Zurich, Zurich, Switzerland.
Chirality plays a critical role in the biochemistry of life and often only one enantiomeric series is observed (homochirality). Only a few natural products have been obtained as racemates, e.g.
View Article and Find Full Text PDFElectroredox N-Heterocyclic Carbene-Catalyzed Enantioselective (3 + 3) Annulation of Enals with 2-Naphthols.
Org Lett
December 2024
Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar, Punjab 140001, India.
Developing asymmetric transformations using electroredox and N-heterocyclic carbene (NHC)-catalyzed radical pathways is still desirable and challenging. Herein, we report an iodide-promoted β-carbon activation (LUMO-lowering process) of enals via electroredox carbene catalysis coupled with a hydrogen evolution reaction (HER). This strategy offers an environmentally friendly and sustainable route for rapidly assembling synthetically useful chiral naphthopyran-3-one in good to excellent yield and enantioselectivity using traceless electrons as inexpensive and greener oxidants.
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!