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[reaction: see text] A Lewis acid-catalyzed formal cycloaddition of alpha,beta-unsaturated aldehydes with 6-methyl-4-hydroxy-2-pyrone, 1,3-diketones, and vinylogous silyl esters is described here.
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http://dx.doi.org/10.1021/ol0523042 | DOI Listing |
Angew Chem Int Ed Engl
December 2024
Xi'an Jiaotong University, Frontier Institute of Science and Technology, 99 Yanxiang road, Yanta district, 710054, Xi'an, CHINA.
Although great advancement has been made in synthesis of 3D bridged bicyclic[n.1.1]-bioisosteres, facile construction of 2D/3D merged molecules incorporating bridged rings, as novel chemical space in drug discovery, remains a significant challenge.
View Article and Find Full Text PDFOrg Lett
December 2024
Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
Catalysts for Claisen rearrangement have been intensively studied to overcome the need for high temperature. However, previous studies have encountered challenges, such as the need for heating, a long reaction time, and/or the need for equivalent amounts of catalyst. In this study, we introduce an effective electrogenerated boron-based Lewis acid catalyst for the aromatic Claisen rearrangement, which proceeds in a few minutes at ambient temperature.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Ruprecht Karls Universitat Heidelberg Fakultat fur Chemie und Geowissenschaften, Organisch-Chemisches Institute, Im Neuenheimer Feld 270, 69120, Heidelberg, GERMANY.
The very first representative of trithia-bridged N-heterotriangulene, a triphenylamine with sulfur atoms bridging the ortho-positions, was synthesized by a sequence of regioselective sulfenylation with phthalimidesulfenyl chloride followed by Lewis acid-catalyzed electrophilic cyclization. X-ray crystallography revealed a saddle-shaped geometry of the polycyclic scaffold. UV/Vis absorption spectroscopy and cyclic voltammetry were used to characterize the optoelectronic properties.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
State Key Laboratory of Chemical Oncogenomics, Institute of Biopharmaceutics and Health Engineering, Tsinghua Shenzhen International Graduate School, Shenzhen 518055, China.
The high percentage of sp-hybridized carbons and the presence of chiral carbon centers could contribute to increased molecular complexity, enhancing the likelihood of clinical success of drug candidates. Three-dimensional (3D) bridged motifs have recently garnered significant interest in medicinal chemistry. Bicyclo[2.
View Article and Find Full Text PDFChemistry
December 2024
Albert-Ludwigs-Universität Freiburg, Institute of Organic Chemistry, Albertstraße 21, 79104, Freiburg, Germany.
A (3+3)-cycloaddition to afford 2-azabiyclo[3.1.1]heptanes was realized by reacting highly strained aryl bicyclo[1.
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