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Chemodivergent 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.
View Article and Find Full Text PDFMicrowave-Assisted Synthesis of Heterocycles via Rhodium(III)-Catalyzed C-H Activation: Norbornadiene as an Acetylene Equivalent.
Org Lett
January 2025
Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States.
General procedures for the rhodium-catalyzed annulation of aryl/heteroaryl -pivaloyl hydroxamic acids and norbornadiene have been developed. Employing norbornadiene as an acetylene equivalent enables utilization of diverse heterocyclic substrates for this transformation which fail to react or undergo competitive Lossen rearrangement under previously reported conditions. Microwave heating significantly reduces reaction times compared to conventional protocols and allows a one-step process to be realized.
View Article and Find Full Text PDFRhodium-Catalyzed Allylic Amination for the Enantioselective Synthesis of Tertiary β-Fluoroamines.
Org Lett
January 2025
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, United States.
The utilization of β-fluoroamines as pharmaceutical components for drug development has attracted a considerable amount of interest. However, direct access to tertiary β-fluoroamines is challenging. We herein report the rhodium-catalyzed asymmetric amination of tertiary allylic trichloroacetimidates with anilines and cyclic aliphatic amines to access tertiary β-fluoroamines, where the α-carbon atom is bonded to four different substituents, in good yield with high levels of enantioselectivity.
View Article and Find Full Text PDFA Formal 1,2-Stevens Rearrangement of Thioester Ylides as a Single-Atom Molecular Editing Tool.
Org Lett
January 2025
University of Belgrade, Faculty of Chemistry, Studentski trg 16, P.O. Box 51, 11158 Belgrade 118, Serbia.
A rhodium-catalyzed reaction of thioesters with diazo reagents was recognized as a powerful and unprecedented tool for single-atom molecular editing by the insertion of a single carbon atom into the C(O)─S thioester bond, thereby leading to various α-thioketones possessing a quaternary carbon atom. A selective and precise defunctionalization of the polyfunctionalized products further demonstrated the synthetic utility of the reaction for the synthesis of more common structural classes of compounds.
View Article and Find Full Text PDFRhodium-catalyzed transformations of diazo compounds a carbene-based strategy: recent advances.
RSC Adv
December 2024
Natural and Medical Sciences Research Center (NMSRC), University of Nizwa Nizwa 616 Sulanate of Oman.
Diazo compounds are known to be good coupling partners in the synthesis of heterocycles, carbocycles and functionalized molecules a rhodium carbene-based strategy. Many heterocyclic and carbocyclic compounds, including isoquinolones and isocoumarins, quinoxalines, indoles, pyrrones, benzothazines, enaminones, benzenes and seven-membered rings, can be constructed using this rhodium-catalyzed system. The reaction mechanism involves C-H activation, carbene insertion and an annulation/functionalization sequence.
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