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Most complex prime links exhibit inherent topological chirality, yet their high stereoinduction remains a rare occurrence. Here, we present a protocol for the stereoselective synthesis of a molecular link comprising two triple entwined rings. We describe steps for constructing the precursor circular helicate, performing ring closure metathesis, and demetallation. We also outline procedures for bio-beads separation and data analysis. This protocol holds promise for applications in molecular nanotopology. For complete details on the use and execution of this protocol, please refer to Zhang et al. (2022)..
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http://dx.doi.org/10.1016/j.xpro.2023.102821 | DOI Listing |
Org Lett
September 2025
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Ahmedabad, Gujarat 382355, India.
Herein, we report an easily tunable and regioselective Pd-catalyzed allene-alkyne coupling protocol for the stereodivergent synthesis of - and -1,3-enynes using purine allenamine by a simple switch of ligands P(-tolyl)Ph and Boc-Phe-OH. For the first time, we have explored mono--protected amino acids (MPAAs) as ligands in allene-alkyne coupling to furnish -1,3-enynes selectively. This protocol streamlined the access to chiral 1,3-enynes and addressed the long-standing stereoselectivity challenges associated with 1,3-enynes from allene-alkyne coupling.
View Article and Find Full Text PDFOrg Lett
September 2025
Institute of Chemistry, Casali Center of Applied Chemistry, The Hebrew University of Jerusalem, Jerusalem 9190401, Israel.
We report a selective dearomative cyclization strategy for the synthesis of 3,4-fused diazabicycles from 3-substituted pyridyl ynamides. The method combines a chemo-, regio-, and stereoselective carbometalation with a regioselective dearomatization, enabling access to a broad range of diazabicyclic scaffolds with varied ring sizes. The protocol accommodates alkyl and aryl Grignard reagents, tolerates diverse functional groups, and supports stereodivergent synthesis, offering a versatile platform for constructing complex fused -heterocycles with potential relevance to medicinal chemistry.
View Article and Find Full Text PDFOrg Lett
September 2025
Flavors and Fragrance Engineering and Technology Research Center of Henan Province, College of Tobacco Science, Henan Agricultural University, Zhengzhou 450046, China.
We developed a photocatalytic copper-catalyzed stereodivergent 3,4-hydroalkoxylation of 1,3-dienes. By simply controlling reaction time, this protocol selectively affords either - or -allylic ethers in moderate to excellent yields with high stereoselectivity (up to >20/1). The transformation demonstrates remarkable scalability, maintaining excellent stereocontrol even at gram-scale operations.
View Article and Find Full Text PDFJ Org Chem
August 2025
Department of Chemistry, SRM University-AP, Amaravati, Andhra Pradesh 522240, India.
An efficient nickel-photoredox dual-catalyzed intermolecular reductive coupling reaction of alkynes with vinyl phosphonates is described. The reaction is highly regio- and stereoselective, affording the homoallylic phosphonates in good to high yields. The present protocol is also successfully applied to other activated alkenes such as enones, acrylates, and vinyl sulfone.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
Dipartimento di Chimica, Università di Torino, via P. Giuria 7, I-10125 Torino, Italy.
Piperidines and their 2-substituted derivatives are fundamental intermediates for the development of new active pharmaceutical ingredients with improved pharmacokinetic profiles and unique three-dimensional properties. Consequently, the design of synthetic methodologies for their selective transformations into highly valuable scaffolds, aimed at increasing the molecular diversity, is of high importance. We disclose herein a general and efficient organolithium-mediated protocol to promote chemo- and regioselective anionic Fries rearrangement or kinetic resolution processes starting from -aryl carbamates of 2-substituted piperidines.
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