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Construction of Axially Chiral Tetra-ortho-Substituted Biaryls by Palladium-Catalyzed Asymmetric Suzuki-Miyaura Coupling.
Chem Asian J
January 2025
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, Jiangsu, China.
Axial chiral biaryl skeletons are widely found in biologically active molecules, catalysts and chiral functional materials. However, highly catalytic stereoselective synthesis of tetra-ortho-substituted biaryls remains a challenging task. In this paper, we describe an efficient approach for construction of axially tetra-ortho-substituted biaryls via Suzuki-Miyaura coupling in the presence of a chiral monophosphate ligand developed by ourselves.
View Article and Find Full Text PDFPalladium-Catalyzed Oxidative Allene-Allene Cross-Coupling.
J Am Chem Soc
January 2025
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.
Direct cross-coupling reactions between two similar unactivated partners are challenging but constitute a powerful strategy for the creation of new carbon-carbon bonds in organic synthesis. [4]Dendralenes are a class of acyclic branched conjugated oligoenes with great synthetic potential for the rapid generation of structural complexity, yet the chemistry of [4]dendralenes remains an unexplored field due to their limited accessibility. Herein, we report a highly selective palladium-catalyzed oxidative cross-coupling of two allenes with the presence of a directing olefin in one of the allenes, enabling the facile synthesis of a broad range of functionalized [4]dendralenes in a convergent modular manner.
View Article and Find Full Text PDFPalladium-Catalyzed Stereospecific Glycosylation Enables Divergent Synthesis of N-O-Linked Glycosides.
Org Lett
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, People's Republic of China.
We present a versatile palladium-catalyzed glycosylation platform that enables facile access to structurally diverse N-O-linked glycosides with constantly excellent regio- and stereoselectivities. Importantly, this approach offers a broad substrate scope, low catalyst loadings, and outstanding chemoselectivity, allowing for the selective reaction of oximes/hydroximic acids over hydroxyl groups that would otherwise pose challenges in conventional glycosylation methods. The synthetic utility of this method is further exemplified through a range of synthetic transformations and late-stage modification of bioactive molecules.
View Article and Find Full Text PDFPalladium-Catalyzed -Allylic Alkylation of Pyrazoles and Unactivated Vinylcyclopropanes.
Org Lett
January 2025
School of Chemistry, Dalian University of Technology, Dalian 116024, P. R. China.
An efficient palladium-catalyzed -allylic alkylation of pyrazoles and unactivated vinylcyclopropanes is demonstrated, affording various -alkyl pyrazoles in ≤99% yield. This protocol displays high atom economy, a broad range of substrates, and excellent regioselectivity and stereoselectivity. Late-stage modification of bioactive molecules, scaled-up reaction, and divergent derivatization documented the practicability of this methodology.
View Article and Find Full Text PDFConcise Asymmetric Total Syntheses of (+)-Dihydropleurotinic Acid and (-)-Pleurotin, Enabling Rapid Late-Stage Diversification.
JACS Au
November 2024
Laboratory of Medicinal Chemical Biology, Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren'ai Road, Suzhou 215123, China.
(-)-Pleurotin () and (+)-dihydropleurotinic acid () are benzoquinone meroterpenoids isolated from fungal sources with powerful antitumor and antibiotic activities. Concise asymmetric total syntheses of the stereochemically pure (+)-dihydropleurotinic acid () and (-)-pleurotin () from the chiral pool ()-Roche ester-derived vinyl bromide have been achieved in 12 and 13 longest linear steps, respectively. The key transformations feature a Michael addition/alkylation cascade reaction to forge three contiguous stereocenters matched with the natural products, a PtO-catalyzed stereoselective reduction of olefin to generate the correct stereocenter at C3, a palladium-catalyzed Negishi cross-coupling between triflate and zinc reagent to introduce the redox-sensitive para-quinone moiety, and a hydroboration/copper-catalyzed carboxylation sequence to incorporate the vital carboxyl group.
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