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Merging Organocatalysis with 1,2-Boronate Rearrangement: A Lewis Base-Catalyzed Asymmetric Multicomponent Reaction.
J Am Chem Soc
October 2024
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, U.K.
Catalytic asymmetric multicomponent 1,2-boronate rearrangements provide a practical approach for synthesizing highly valuable enantioenriched boronic esters. When applied to alkenyl or heteroaryl boronates, these reactions have relied mainly on transition-metal catalysis. Herein, we present an organocatalytic, Lewis base-catalyzed asymmetric multicomponent 1,2-boronate rearrangement, involving indoles, boronic esters, and Morita-Baylis-Hillman carbonates, leading to enantioenriched, highly substituted indole and indoline derivatives.
View Article and Find Full Text PDFN-Heterocyclic Carbene/Transition Metal Dual Catalysis.
Chemistry
September 2024
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
N-heterocyclic carbene catalysis has been developed as a versatile method for the enantioselective synthesis of complex organic molecules in organic chemistry. Merging of N-heterocyclic carbene catalysis with transition metal catalysis holds the potential to achieve unprecedented transformations with broad substrate scope and excellent stereoselectivity, which are unfeasible with individual catalyst. Thus, this dual catalysis has attracted increasing attention, and numerous elegant dual catalytic systems have been established.
View Article and Find Full Text PDFMerging of Palladium and Organocatalysis Enabled Asymmetric Decarboxylative (2+1) Cycloadditions toward Cyclopropanes.
Org Lett
May 2024
Frontier Institute of Science and Technology (FIST), Xi'an Jiaotong University, Xi'an 710049, China.
A cascade reaction enabling enantio- and diastereoselective construction of strained cyclopropanes is described. This asymmetric (2+1) annulation process uses vinyl methylene carbonate and 2-cyanoacrylate as reaction partners in the presence of Pd(PPh) as a precatalyst and an enantioenriched phosphoramidite ligand featuring a morpholine functionality. Mechanistic investigations unveil that the PPh derived from the Pd(PPh) and the morpholine-containing phosphoramidite work as cooperative phosphorus and Brønsted base catalysts to promote the reaction.
View Article and Find Full Text PDFEnantioselective merged gold/organocatalysis.
Chem Commun (Camb)
March 2024
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal-462066, India.
Gold complexes, because of their unique carbophilic nature, have evolved as efficient catalysts for catalyzing various functionalization reactions of C-C multiple bonds. However, the realization of enantioselective transformations gold catalysis remains challenging due to the geometrical constraints and coordination behaviors of gold complexes. In this context, merged gold/organocatalysis has emerged as one of the intriguing strategies to achieve enantioselective transformations which could not be possible by using a single catalytic system.
View Article and Find Full Text PDFMerging gold plasmonic nanoparticles and L-proline inside a MOF for plasmon-induced visible light chiral organocatalysis at low temperature.
Nanoscale
March 2024
Department of Solid State Engineering, University of Chemistry and Technology, 16628 Prague, Czech Republic.
Light-driven asymmetric photocatalysis represents a straightforward approach in modern organic chemistry. In comparison to the homogeneous one, heterogeneous asymmetric photocatalysis has the advantages of easy catalyst separation, recovery, and reuse, thus being cost- and time-effective. Here, we demonstrate how plasmon-active centers (gold nanoparticles - AuNPs) allow visible light triggering of chiral catalyst (proline) in model aldol reaction between acetone and benzaldehyde.
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