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Alkoxy-Directed Dienamine Catalysis in [4 + 2]-Cycloaddition: Enantioselective Synthesis of Benzo-[3]-ladderanol.
J Am Chem Soc
January 2025
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Despite tremendous progress of dienamine catalysis along with its application in enantioselective synthesis over nearly two decades, certain limitations, especially with respect to the regioselectivity in the dienamine generation step, continue to persist. To overcome these shortcomings of classical dienamine catalysis, we now introduce the concept of alkoxy-directed dienamine catalysis and apply it to the enantioselective arene construction by desymmetrizing -enediones through [4 + 2]-cycloaddition. Catalyzed by a diphenylprolinol silyl ether, this reaction utilizes γ-alkoxy α,β-unsaturated aldehydes as the substrate and proceeds in a highly regioselective fashion through the intermediacy of δ-alkoxy dienamine.
View Article and Find Full Text PDFCatalytic Asymmetric 1,4-Hydrocarbonation of 1,3-Enynes via Photoredox/Cobalt/Chromium Triple Catalysis.
Angew Chem Int Ed Engl
January 2025
Shanghai Jiao Tong University, Chemistry, 800 Dongchuan RD. Minhang District, 200240, Shanghai, CHINA.
A synergistic photoredox/cobalt/chromium triple catalysis system for regioselective, enantioselective, and diastereoselective 1,4-hydrocarbonation of readily available 1,3-enyne precursors was explored, providing a modular synthetic platform for various trisubstituted axially chiral allenes bearing an extra central chirality. The protocol features a broad substrate scope, good functional group tolerance, excellent selectivity, and mild reaction conditions. Furthermore, a possible reaction mechanism is proposed based on numerous control experiments and density functional theory calculations.
View Article and Find Full Text PDFOrganocatalytic Enantioselective Friedel-Crafts Reaction of Phenanthrenequinones and Indoles.
Molecules
January 2025
Department of Pharmacy, Jilin Medical University, Jilin 132013, China.
An efficient stereoselective synthesis of 10-hydroxy-10-(1-indol-3-yl)-9-(10)-phenanthrene derivatives was realized through an organocatalyzed Friedel-Crafts reaction of phenanthrenequinones and indoles using a (,)-dimethylaminocyclohexyl-squaramide as the catalyst. Under the optimized conditions, the desired chiral products were obtained in good yields (73-90%) with moderate to high ee values (up to 97% ee). Two pairs of synthesized enantiomers were subjected to evaluation of their antiproliferative activities on four types of human cancer cell lines and one human umbilical vein endothelial cell line using the CCK-8 assay.
View Article and Find Full Text PDFEnzymatic Cascades for Stereoselective and Regioselective Amide Bond Assembly.
Angew Chem Int Ed Engl
January 2025
The University of Manchester, School of Chemistry & Manchester Institute of Biotechnology, 131 Princess Street, M1 7DN, Manchester, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
Amide bond formation is fundamental in nature and is widely used in the synthesis of pharmaceuticals and other valuable products. Current methods for amide synthesis are often step and atom inefficient, requiring the use of protecting groups, deleterious reagents and organic solvents that create significant waste. The development of cleaner and more efficient catalytic methods for amide synthesis remains an urgent unmet need.
View Article and Find Full Text PDFChemodivergent and Enantioselective Synthesis of Spirobi[dihydrophenalene] Structures.
Org Lett
January 2025
Department of Chemistry, School of Science, China Pharmaceutical University, Nanjing 211198, People's Republic of China.
The development and enantioselective synthesis of two types of -symmetric spirobi[dihydrophenalene] structures is reported. The reaction proceeds via rhodium-catalyzed 2-fold asymmetric conjugate arylation of dienones followed by BF·OEt-promoted spirocyclization to give the enantiopure spiro products. Additive-dependent chemodivergent synthesis of 3,3'-diarylated 2,2',3,3'-tetrahydro-1,1'-spirobi[phenalene]-9,9'-diols (3,3'-Ar-SPHENOLs) and the corresponding spiro diary ethers from the same intermediate is achieved.
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