A new one-pot domino reaction for a general entry to functionalised bridged bicyclo[n.2.1] ring systems from alpha, alpha'-diactivated cyclic ketones and trans-1,4-dihalides is described. The sequence combines a base promoted C-O cycloalkylation reaction leading to fused polycyclic enol ethers and their in situ palladium-catalysed isomerisation.
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http://dx.doi.org/10.1007/s11030-009-9131-2 | DOI Listing |
Org Biomol Chem
October 2024
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Here we report a three-component reaction of 2-formylarylboronic acids, -sulfonyl amines and 1,3-enynes, proceeding through a cascade imine formation/Pd-catalysed vinylogous addition/intramolecular Suzuki coupling/isomerization process. This protocol exhibited broad substrate scope and good functionality tolerance, and a spectrum of multifunctionalised benzofulvene derivatives were furnished in moderate to good yields and /-selectivity.
View Article and Find Full Text PDFCommun Chem
October 2023
Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
Spirocyclic tetrahydronaphthyridines (THNs) are valuable scaffolds for drug discovery campaigns, but access to this 3D chemical space is hampered by a lack of modular and scalable synthetic methods. We hereby report an automated, continuous flow synthesis of α-alkylated and spirocyclic 1,2,3,4-tetrahydro-1,8-naphthyridines ("1,8-THNs"), in addition to their regioisomeric 1,6-THN analogues, from abundant primary amine feedstocks. An annulative disconnection approach based on photoredox-catalysed hydroaminoalkylation (HAA) of halogenated vinylpyridines is sequenced in combination with intramolecular SAr N-arylation.
View Article and Find Full Text PDFNat Chem
July 2023
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, China.
Direct and selective functionalization of hydrocarbon chains is a fundamental problem in synthetic chemistry. Conventional functionalization of C=C double bonds and C(sp)-H bonds provides some solutions, but site diversity remains an issue. The merging of alkene isomerization with (oxidative) functionalization provides an ideal method for remote functionalization, which would provide more opportunities for site diversity.
View Article and Find Full Text PDFChem Commun (Camb)
June 2022
Departamento de Química Orgánica, Universidad de Sevilla, C/Prof. García González, 1, 41012 Sevilla, Spain.
A palladium-catalyzed asymmeric conjugate addition of aryl boronic acids to medium-sized cycloalkenones followed by intramolecular aldol trapping is reported. The use of formed [Pd/(QuinoxP*)] as the catalyst enables the synthesis of arylbicyclic scaffolds in good yields and with excellent stereocontrol (up to 7 : 1 dr, up to 99% ee). The reaction is applicable to a range of medium size ketoenone substrates and funcionalized aryl boronic acids, including heterocyclic compounds.
View Article and Find Full Text PDFChemistry
December 2021
Chang-Kung Chuang Institute, Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, No. 500, Dongchuan Road, Shanghai, 200241, China.
Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.
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