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Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ-Butyrolactam.
J Org Chem
December 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China.
A palladium-catalyzed asymmetric chlorocyclization of 1,6-enynes has been described. Controlling the chloride ion concentration in the system by substrate design is the key to achieving asymmetric chlorinated cyclization. In the presence of Pd(PhCN)Cl and chiral phosphoramidite ligands, the reaction accesses diverse chiral ()-α-chloromethylene-γ-butyrolactams with excellent selectivity and enantioselectivity.
View Article and Find Full Text PDFChiral metal clusters, due to their intriguing optical properties and unique resemblance in size to biomolecules, have attracted a lot of attention in recent times as potential candidates for application in bio-detection and therapy. While several strategies are reported for the synthesis of optically active clusters, a facile approach that enhances a multitude of properties has remained a challenge. Herein, we report a simple strategy wherein the use of a chiral cationic surfactant, during the synthesis of achiral clusters, leads to the fabrication of chiral assemblies possessing enhanced luminescence and optical activity.
View Article and Find Full Text PDFChiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of 2,2-Disubstituted 2,3-Dihydro-4-quinolones from Isatins and 2'-Aminoacetophenones.
Org Lett
December 2024
Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Herein, we present the enantioselective synthesis of 2,3-dihydro-4-quinolones bearing chiral tetrasubstituted carbons from isatins and 2'-aminoacetophenones. The transformation is mediated by a chiral phosphoric acid catalyst and proceeds via an generated ketimine and subsequent enantioselective intramolecular cyclization. The methodology features a broad scope and functional group tolerance with yields and enantioselectivities of up to 99% and 98% ee.
View Article and Find Full Text PDFEnantioselective Vinylogous Addition of Enones to Allenes Enabled by Synergistic Borane/Palladium Catalysis.
J Am Chem Soc
December 2024
State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China.
Herein, we report a method for enantioselective vinylogous addition of enones to alkoxyallenes enabled by synergistic borane/palladium catalysis. The inductive effect provided by borane coordination to the ketone was essential for closing the gap between the conditions needed for the generation of a dienolate and those needed for initiation of the palladium catalytic cycle by protonation of the metal catalyst. Furthermore, we accomplished the first example of stereodivergent synthesis with chiral borane/transition-metal catalysts.
View Article and Find Full Text PDFEnantioselective Synthesis of Isoindolinone by Sequential Palladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction.
Org Lett
December 2024
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
We present a tandem aza-Heck/Suzuki cross-coupling reaction of -phenyl hydroxamic ethers with readily available arylboronic and alkenyl boronic acids. This protocol is enabled by a palladium catalyst paired with chiral phosphoramidite ligands, particularly under mild reaction conditions, yielding efficient and succinct synthetic routes to chiral isoindolinones with high enantioselectivity. Furthermore, this reaction exhibits excellent functional group compatibility and a rich diversity of subsequent transformations.
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