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http://dx.doi.org/10.1002/cbic.201000422 | DOI Listing |
Chempluschem
January 2025
University of Vienna, Faculty of Chemistry, Währinger Str. 17, 1090, Vienna, AUSTRIA.
The Lewis acid-catalyzed coupling of alkenes and aldehydes presents a modern, versatile synthetic alternative to classical carbonyl addition chemistry, offering exceptional regio- and stereoselectivity. In this work, we present a comprehensive computational investigation into the reaction mechanism of this transformation. Our findings confirm the occurrence of an enantioselective trans-annular [1,5]-hydride shift step and demonstrate that the enantioselectivity of the reaction arises predominantly from steric clashes between functional groups in the cyclization step.
View Article and Find Full Text PDFCurr Org Synth
January 2025
School of Chemistry and Chemical Engineering, Changsha University of Science and Technology, Changsha, 410114, China.
Nitrogen-containing heterocycles, such as indoles and quinolines, serve as the key scaffolds in numerous pharmaceuticals, pesticides, and natural products. The synthesis methods of nitrogen-containing heterocycles show significant scientific and industrial value. As a chemical intermediate featuring dual functional groups, cyanamide plays a crucial role in organic synthesis, directly affecting the development of new drugs and the design of new materials.
View Article and Find Full Text PDFOrg Lett
January 2025
Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
Herein, a -phenylphenothiazine-based hyper-cross-linked polymer (PTH-HCP) was finely designed and constructed, which serves as a metal-free heterogeneous photocatalyst for organic transformations. Characterization experiments have shown that this polymer demonstrates outstanding stability, extensive surface area, and exceptional photoelectric response properties. Moreover, PTH-HCP showed good catalytic efficiency and recyclability in the photochemically driven difluoromethylation/cyclization reactions.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Chiral medium-sized rings, albeit displaying attractive properties for drug development, suffer from numerous synthetic challenges due to difficult cyclization steps that must take place to form these unusually strained, atropisomeric rings from sterically crowded precursors. In fact, catalytic enantioselective cyclization methods for the formation of chiral seven-membered rings are unknown, and the corresponding eight-membered variants are also sparse. In this work, we present a substrate preorganization-based, enantioselective, organocatalytic strategy to construct seven- and eight-membered rings featuring chirality that is intrinsic to the ring in the absence of singular stereogenic atoms or single bond axes of chirality.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
University of Amsterdam Van 't Hoff Institute for Molecular Sciences: Universiteit van Amsterdam Van 't Hoff Institute for Molecular Sciences, HIMS, NETHERLANDS, KINGDOM OF THE.
The complexity of allosteric enzymatic regulation continues to inspire synthetic chemists seeking to emulate interconnected biological systems. In this work, a Pt2L4 cage capable of catalyzing the cyclization reaction of an alkynoic tosyl amide is orthogonally coupled to a diacid-catalyzed carbodiimide-hydration cycle. This new Pt-catalyzed cyclization reaction is demonstrated to exhibit electronic regulation by inclusion of different guest effectors.
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