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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 PDFStereocontrol of C-N Axial and Spiro-Central Chirality via Rh(II)-Catalyzed Enantioselective N-H Bond Insertion of Indolinone-Spiroacetal.
Org Lett
October 2023
Institute of Medicinal Plant Development, Chinese Academy of Medical Science and Peking Union Medical College, Beijing 100193, China.
Article Synopsis
- A new rhodium-catalyzed method is introduced for carbene N-H insertion that effectively controls both C-N axial and spiro-central chiralities, leading to the creation of enantiopure -arylindolinone-spiroacetal derivatives.
- This strategy showcases high yields and excellent enantioselectivities, offering potential for functional group tolerance and late-stage diversification in chemical synthesis.
- Density Functional Theory (DFT) calculations suggest that the N-H insertion is pivotal for determining axial chirality, while a 1,5-hydrogen shift is specifically influenced by the spirocycle structure.
Construction of C2-Quaternary-indol-3-ones via Rh-Catalyzed [3+2] Spirocyclization from Indole Ketones and Nitroolefins.
J Org Chem
May 2022
College of Chemistry and Material Science, Sichuan Normal University, Chengdu 610066 Sichuan, China.
Novel complex C2-quaternary-indol-3-one units bearing versatile nitro groups have been successfully developed from pseudo-indolones and α,β-unsaturated nitroolefins through rhodium-catalyzed C-H activation/[3 + 2] spirocyclization. Notably, four diastereomers could be selectively obtained in the reaction by condition control.
View Article and Find Full Text PDFElectrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations.
Chem Sci
March 2022
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen Tammannstraße 2 37077 Göttingen Germany
Despite indisputable progress in the development of electrochemical transformations, electrocatalytic annulations for the synthesis of biologically relevant three-dimensional spirocyclic compounds has as of yet not been accomplished. In sharp contrast, herein, we describe the palladaelectro-catalyzed C-H activation/[3 + 2] spiroannulation of alkynes by 1-aryl-2-naphthols. Likewise, a cationic rhodium(iii) catalyst was shown to enable electrooxidative [3 + 2] spiroannulations formal C(sp)-H activations.
View Article and Find Full Text PDFEnantioselective Synthesis of Spiro-oxiranes: An Asymmetric Addition/Aldol/Spirocyclization Domino Cascade.
Angew Chem Int Ed Engl
September 2021
Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S 3H6, Canada.
Enantioenriched spiro-oxiranes bearing three contiguous stereocenters were synthesized using a rhodium-catalyzed asymmetric addition/aldol/spirocyclization sequence. Starting from a linear substrate, the cascade enabled the formation of a spirocyclic framework in a single step. sp - and sp-hybridized carbon nucleophiles were found to be competent initiators for this cascade, giving arylated or alkynylated products, respectively.
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