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Palladium-catalyzed allylic C-H alkylation of terminal olefins with 3-carboxamide oxindoles.
Org Biomol Chem
January 2025
Chongqing Research Center for Pharmaceutical Engineering, College of Pharmacy, Chongqing Medical University, Chongqing 400016, China.
A novel palladium-catalyzed allylic C-H alkylation of terminal olefins with 3-carboxamide oxindoles is described. A variety of new 3-carboxamide-3-allylation oxindoles with an all-carbon quaternary center were obtained in moderate to good yields (up to 99%). In addition, the asymmetric version of this reaction was also explored, providing moderate enantioselectivity.
View Article and Find Full Text PDFSynthesis of Chiral Saturated Heterocycles Bearing Quaternary Centers via Enantioselective β-C(sp)-H Activation of Lactams.
J Am Chem Soc
January 2025
Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
The development of catalytic methods for the synthesis of enantiopure saturated heterocycles has been a long-standing challenge in asymmetric catalysis. We describe the first highly enantioselective palladium-catalyzed βC(sp)-H arylation and olefination of lactams for the preparation of various chiral N-heterocycles bearing quaternary carbon centers. The presence of strongly electron-withdrawing groups on the chiral bifunctional MPAThio ligand is crucial to the reactivity of weakly coordinating lactams.
View Article and Find Full Text PDFCatalytic asymmetric C-N cross-coupling towards boron-stereogenic 3-amino-BODIPYs.
Nat Commun
January 2025
Shenzhen Grubbs Institute and Department of Chemistry, Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong, China.
3-Amino boron dipyrromethenes (BODIPYs) are a versatile class of fluorophores widely utilized in live cell imaging, photodynamic therapy, and fluorescent materials science. Despite the growing demand for optically active BODIPYs, the synthesis of chiral 3-amino-BODIPYs, particularly the catalytic asymmetric version, remains a challenge. Herein, we report the synthesis of boron-stereogenic 3-amino-BODIPYs via a palladium-catalyzed desymmetric C-N cross-coupling of prochiral 3,5-dihalogen-BODIPYs.
View Article and Find Full Text PDFPalladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ-Butyrolactam.
J Org Chem
January 2025
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 PDFSynthesis of Optically Active Spirocycles by a Sequence of Decarboxylative Asymmetric Allylic Alkylation and Heck Reaction.
Org Lett
December 2024
Institut für Chemie, Universität Oldenburg, D-26129 Oldenburg, Germany.
Optically active spirocycles were prepared in a sequence of two palladium-catalyzed reactions. In the first step, racemic α-(-iodophenyl)-β-oxo allyl esters were submitted to the palladium-catalyzed decarboxylative asymmetric allylic alkylation reaction, furnishing the α-allylated products with a quaternary stereocenter with good yields and enantioselectivities. Subsequently, these intermediate products were converted in a Heck reaction yielding the spirocyclic structures as a mixture of - and -cyclic regioisomers.
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