Novel enantiopure policyclic nitrogen heterocycles have been obtained in the diastereoselective aza-Diels-Alder or Mannich reaction of dienes with imine formed in situ from ethyl glyoxylate and (1R,2R)-diaminocyclohexane.
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http://dx.doi.org/10.1021/jo302820m | DOI Listing |
Org Lett
December 2024
School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, Taizhou, 318000 Zhejiang, China.
We herein report a switchable coupling of acrylic acids with ethyl glyoxylate under ruthenium catalysis enabling the synthesis of diverse functionalized γ-butenolides. The carboxyl-directed vinylic C-H cleavage and dual nucleophilic addition to aldehyde are achieved to deliver hydroxymethylated butanolides under mild and oxidant-free conditions. Alternatively, a controlled and unprecedented tandem C-H cyclization/oxidative homocoupling reaction is realized by using silver salt as the oxidant to generate a range of dimeric butenolides bearing vicinal all-carbon quaternary centers.
View Article and Find Full Text PDFMolecules
September 2024
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
The reaction between glycine-type aminonaphthol derivatives substituted with 2- or 1-naphthol and indole or 7-azaindole has been tested. Starting from 2-naphthol as a precursor, the reaction led to the formation of ring-closed products, while in the case of a 1-naphthol-type precursor, the desired biaryl ester was isolated. The synthesis of a bifunctional precursor starting from 5-chloro-8-hydroxyquinoline, morpholine, and ethyl glyoxylate via modified Mannich reaction is reported.
View Article and Find Full Text PDFInorg Chem
May 2024
Key Lab of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. China.
Transition-metal-catalyzed, strain-release-driven transformations of "spring-loaded" bicyclo[1.1.0]butanes (BCBs) are considered potent tools in synthetic organic chemistry.
View Article and Find Full Text PDFSmall
July 2024
Université de Haute-Alsace, CNRS, IS2M UMR7361, Mulhouse, F-68100, France.
Investigations concerning the glyoxylate moiety as a photocleavable functional group for visible light photoinitiators, particularly in the initiation of free radical photopolymerization remain limited. This study introduces nine innovative carbazole-based ethyl glyoxylate derivatives (CEGs), which are synthesized and found to exhibit excellent photoinitiation abilities as monocomponent photoinitiating systems. Notably, these structures demonstrate robust absorption in the near-UV/visible range, surpassing the commercial photoinitiators.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
March 2024
Key Centre for Polymers and Colloids, School of Chemistry, The University of Sydney, 2006, Sydney, NSW, Australia.
Polymer nanodiscs, especially with stimuli-responsive features, represent an unexplored frontier in the nanomaterial landscape. Such 2D nanomaterials are considered highly promising for advanced biomedicine applications. Herein, we designed a rod-coil copolymer architecture based on an amphiphilic, tadpole-like bottlebrush copolymer, which can directly self-assemble into core-shell nanodiscs in an aqueous environment.
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