99802-91-2

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 19202-21-2 3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 80783-99-9 3-phenyl-N-methoxy-N-methylacrylamide 
• 621-82-9 Cinnamic acid 
• 85692-37-1 1-(1-methyl-1H-imidazol-2-yl)ethan-1-one 
• 100-52-7 benzaldehyde 
• 102-92-1 cinnamoyl chloride 
• 860772-73-2 1-(1-methyl-1H-imidazole-2-yl)-2-(triphenylphosphoranylidene)-ethanone 

Downstream Products

• 1227008-95-8 (2S,3S)-methyl 2-hydroxy-5-(1-methyl-1H-imidazol-2-yl)-5-oxo-2,3-diphenylpentanoate 
• 1227009-09-7 (2S,3S)-methyl 2-hydroxy-2-(4-methoxyphenyl)-5-(1-methyl-1H-imidazol-2-yl)-5-oxo-3-phenylpentanoate 
• 1224854-19-6 3-(5-methoxy-1H-indole-3-yl)-1-(1-methyl-1H-imidazol-2-yl)-3-phenylpropan-1-one 
• 1185267-52-0 dimethyl 2-(3-(1-methyl-1H-imidazol-2-yl)-3-oxo-1-phenylpropyl)malonate 
• 1242049-85-9 1-(1-methyl-1H-imidazol-2-yl)-3-(1-methyl-1H-indol-3-yl)-3-phenylpropan-1-one 
• 1242049-81-5 3-(5-methoxy-1H-indol-3-yl)-1-(1-methyl-1H-imidazol-2-yl)-3-phenyl-1-propanone 
• 1007843-89-1 (S)-1-(1-methyl-1H-imidazol-2-yl)-4-nitro-3-phenylbutan-1-one 
• 1007843-83-5 2-[3-(1-methyl-1H-imidazol-2-yl)-3-oxo-1-phenyl-propyl]-malonic acid dimethyl ester 

Relevant academic research and scientific papers

Asymmetric [3 + 2] Cycloaddition Employing N, N′-Cyclic Azomethine Imines Catalyzed by Chiral-at-Metal Rhodium Complex

An efficient asymmetric 1,3-dipolar cycloaddition of α,β-unsaturated 2-acyl imidazoles with N,N′-cyclic azomethine imines catalyzed by a chiral-at-metal rhodium complex is reported. The corresponding N,N′-bicyclic pyrazolidine derivatives with three conti

Chiral-at-Metal Rh(III) Complex Catalyzed Asymmetric Conjugate Addition of Unactivated Alkenes with α,β-Unsaturated 2-Acyl Imidazoles

A newly prepared chiral-at-metal Rh(III) complex catalyzed highly efficient asymmetric conjugate addition of para-vinylanilines with α,β-unsaturated 2-acyl imidazoles is developed, affording the corresponding adducts in 67-95% yields with 86-95% ee. Remarkably, employing as low as 0.05 mol % of Rh(III) complex as catalyst, a gram-scale reaction still affords the desired product in 81% yield with 92% ee.

Cooperative Lewis Acid Catalysis for the Enantioselective C(sp3)-H Bond Functionalizations of 2-Alkyl Azaarenes

Herein, we describe the enantioselective C(sp3)-H bond functionalizations of 2-alkyl azaarenes using a cooperative dual Lewis acid catalysis. An achiral Lewis acid activates the unactivated azaarene partner without the need for a strong base. Orthogonally, a chiral-at-metal Lewis acid catalyst enables LUMO lowering and induces chirality. This method tolerates a range of complex molecular scaffolds and exhibits good to excellent yields and selectivity while accepting a wide variety of functional groups.

Modular Design of G-Quadruplex MetalloDNAzymes for Catalytic C-C Bond Formations with Switchable Enantioselectivity

Metal-binding DNA structures with catalytic function are receiving increasing interest. Although a number of metalloDNAzymes have been reported to be highly efficient, the exact coordination/position of their catalytic metal center is often unknown. Here, we present a new approach to rationally develop metalloDNAzymes for Lewis acid-catalyzed reactions such as enantioselective Michael additions. Our strategy relies on the predictable folding patterns of unimolecular DNA G-quadruplexes, combined with the concept of metal-mediated base-pairing. Transition-metal coordination environments were created in G-quadruplex loop regions, accessible by substrates. Therefore, protein-inspired imidazole ligandoside L was covalently incorporated into a series of G-rich DNA strands by solid-phase synthesis. Iterative rounds of DNA sequence design and catalytic assays allowed us to select tailored metalloDNAzymes giving high conversions and excellent enantioselectivities (≥99%). Based on their primary sequence, folding pattern, and metal coordination mode, valuable information on structure-activity relationships could be extracted. Variation of the number and position of ligand L within the sequence allowed us to control the formation of (S) and (R) enantiomeric reaction products, respectively.

Asymmetric Synthesis of Multi-Substituted Tetrahydrofurans via Palladium/Rhodium Synergistic Catalyzed [3+2] Decarboxylative Cycloaddition of Vinylethylene Carbonates

Unlike the comprehensive development of tandem multi-metallic catalysis, bimetallic synergistic catalysis has been challenging to achieve high stereoselectivity with the generation of multi-stereogenic centers. Herein, an efficient synergistic catalysis for the diastereo- and enantioselective synthesis of multi-substituted tetrahydrofuran derivatives has been developed. Under mild reaction conditions, a series of target molecules with three consecutive stereocenters were synthesized by a palladium(0)/rhodium(III) bimetal-catalyzed asymmetric decarboxylative [3+2]-cycloaddition of vinylethylene carbonates with α,β-unsaturated carbonyl compounds. The corresponding adducts were obtained with moderate to high yields (67 %～98 %) and excellent stereoselectivities (>20 : 1 d.r., up to 99 % ee).

Guanosine-based self-assembly as an enantioselective catalyst scaffold

A self-assembled G-quadruplex formed by guanosine and borate as the chiral scaffold was used to catalyze the asymmetric Friedel-Crafts reaction in water. Catalysis, depending on the self-assembly of guanosine and borate into a fibrillar structure in the p

Enantioselective Synthesis of Multisubstituted Spirocyclopentane Oxindoles Enabled by Pd/Chiral Rh(III) Complex Synergistic Catalysis

An asymmetric [3 + 2]-cycloaddition reaction of α,β-unsaturated 2-acyl imidazoles with spirovinylcyclopropanyl-2-oxindoles catalyzed synergistically by an achiral palladium(0) catalyst and a chiral-at-metal rhodium(III) complex has been developed. A series of biologically important 3-spirocyclopentane-2-oxindoles with four contiguous stereocenters were synthesized in high yields (up to 99%) with excellent stereoselectivities (up to 99% ee, 20:1 dr).

Enantioselective Mukaiyama–Michael Reaction Catalyzed by a Chiral Rhodium Complex Based on Pinene-Modified Pyridine Ligands

The rhodium complex Λ-Rh1 containing chiral pinene-modified pyridine ligands is prepared through a two-step synthetic procedure; it exhibits excellent reactivity and enantiocontrol towards the enantioselective Mukaiyama–Michael reaction of α,β-unsaturated 2-acyl imidazoles with silyl enol ethers, affording enantioenriched 1,5-dicarbonyl compounds in good yields (up to 99 %) with excellent enantioselectivities (up to 99 % ee).

Enantioselective 2-alkylation of 3-substituted indoles with dual chiral lewis acid/hydrogen-bond-mediated catalyst

A chiral-at-metal bis-cyclometalated iridium complex combines electrophile activation via metal coordination with nucleophile activation through hydrogen bond formation. This new bifunctional chiral Lewis acid/hydrogenbond-mediated catalyst permits the challenging enantioselective 2-alkylation of 3-substituted indoles with α, β-unsaturated 2-acyl imidazoles in up to 99% yield and with up to 98% enantiomeric excess at a catalyst loading of 2 mol %. As an application, the straightforward synthesis of a chiral pyrrolo- [1, 2-a]indole is demonstrated.

A visible-light-activated rhodium complex in enantioselective conjugate addition of α-amino radicals with Michael acceptors

We report an efficient enantioselective conjugate addition of photogenerated α-amino radicals to Michael acceptors catalyzed by a newly prepared chiral-at-metal rhodium complex. This protocol shows that a single Rh(iii) complex can serve not only as a Lewis acid but also as a photoredox catalyst to control the stereoselectivity during the bond formation.