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A highly diastereoselective annulation of simple aldehydes and 5-alkenyl thiazolones, via oxidative NHC catalysis has been developed. This strategy provides facile access to a diverse library of functionalized chiral thiazolo pyrones. Aerobic oxygen can also be applied as a secondary oxidant to avoid the use of stoichiometric organic or inorganic oxidants.
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http://dx.doi.org/10.1039/c5cc01587a | DOI Listing |
Org Lett
September 2025
Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs. College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China.
In this work, we report a novel I-mediated ring-opening -difunctionalization of cyclopropyl alcohols with enaminones for the first time. The selective [3 + 2] annulation instead of [3 + 3] annulation under metal-free conditions enables a straightforward and efficient synthesis of structurally important 2,4-diacylpyrroles. Notably, this methodology dispenses with metal catalysts, proceeds under mild reaction conditions, and features not only simple operation but also suitability for gram-scale preparation and late-stage functionalization of complex bioactive molecules.
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August 2025
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, China.
A significant advancement has been made in the dimerization and cyclization of styrenes in one step to construct nitrogen-containing heterocyclic skeletons. Herein, we report a novel [2+2+1] dimerization annulation of styrenes and TMSN via Schmidt rearrangement, enabling straightforward access to 1-pyrrolines from the most easily available materials. Different from 5--trig cyclization, this strategy not only obviated the needs of an oxidant, a metal, and presynthesis but also possessed simple and green operations.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM, USA.
A novel, annulative endoperoxidation of tetronate derivatives bearing unsaturated side chains is presented. The reaction requires a simple setup and proceeds under mild conditions to generate tricyclic endoperoxides in modest diastereoselectivities and useful yields. A free-radical mechanism is proposed.
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August 2025
Innovation Team of Optical Functional Molecular Devices, Inner Mongolia Key Laboratory for the Natural Products Chemistry and Functional Molecular Synthesis, College of Chemistry and Materials Science, Inner Mongolia Minzu University, Tongliao 028000, China.
A base-controlled rhodium(III)-catalyzed regioselective C-H alkylation and annulation of 2-arylindoles with α-Cl ketones in a single catalytic system is described, in which α-Cl ketones serve as C(sp)-based electrophilic partners and oxidized alkyne equivalents. When using NaOAc as the base, the C-H functionalization selectively delivered 1-aryl-2-(2-aryl-1-indol-3-yl)ethan-1-ones. In contrast, the same catalytic system with the base NaHCO predominately provided 5-aryl-11-benzo[]carbazoles.
View Article and Find Full Text PDFJ Org Chem
August 2025
Collaborative Innovation Center for Advanced Organic Chemical Materials Co-Constructed by the Province and Ministry, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei Key Laboratory for Precision Synthesis of Small Molecule Pharmaceuticals,
We report a cobalt-catalyzed cascade [4 + 2] annulation of the C(sp)-H/N-H bonds in indolecarboxamides with alkenes, facilitated by an 8-aminoquinoline directing group. This reaction represents the first example employing simple olefins as substrates to directly construct the γ-carbolinone motif. Furthermore, it exhibits broad substrate scope and excellent regioselectivity, achieving high yields with various unactivated alkenes, even bulky octadecene.
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