54673-12-0

Upstream product

• 13057-17-5 bromethyl methyl ether 
• 60-12-8 2-phenylethanol 
• 103-82-2 phenylacetic acid 
• 105104-40-3 Okahara's reagent 
• 109-87-5 Dimethoxymethane 
• 107-30-2 chloromethyl methyl ether 
• 82529-79-1 4-methoxybenzyl phenethyl ether 
• 3587-61-9 1-chloromethyl 2-phenylethyl ether 
• 124-41-4 sodium methylate 

Downstream Products

• 17376-04-4 2-phenethyl iodide 
• 103-63-9 1-phenyl-2-bromoethane 
• 645-59-0 dihydrocinnamonitrile 
• 493-05-0 isochromane 
• 1355017-07-0 C₁₇H₁₄O 
• 1338236-26-2 C₁₇H₁₄O 
• 1338236-27-3 C₁₈H₁₆O 
• 1338236-28-4 C₁₈H₁₆O 
• 1338236-29-5 C₁₈H₁₆O 
• 1338236-30-8 C₁₉H₁₈O 
• 1338236-31-9 C₁₈H₁₃F₃O 
• 1338236-32-0 C₂₀H₁₈O₃ 
• 1338236-33-1 C₁₇H₁₃FO 
• 1338236-34-2 C₁₈H₁₆O₂ 

Relevant academic research and scientific papers

Iridium-Catalyzed Enantioselective Hydrogenation of Oxocarbenium Ions: A Case of Ionic Hydrogenation

Ionic hydrogenation has not been extensively explored, but is advantageous for challenging substrates such as unsaturated intermediates. Reported here is an iridium-catalyzed hydrogenation of oxocarbenium ions to afford chiral isochromans with high enantioselectivities. A variety of functionalities are compatible with this catalytic system. In the presence of a catalytic amount of the Br?nsted acid HCl, an α-chloroether is generated in situ and subsequentially reduced. Kinetic studies suggest first-order kinetics in the substrate and half-order kinetics in the catalyst. A positive nonlinear effect, together with the half kinetic order, revealed a dimerization of the catalyst. Possible reaction pathways based on the monomeric iridium catalyst were proposed and DFT computational studies revealed an ionic hydrogenation pathway. Chloride abstraction and the cleavage of dihydrogen occur in the same step.

Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles

The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf)3 and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.

Enantioselective synthesis of tetrahydroisoquinoline derivatives via chiral-at-metal rhodium complex catalyzed [3+2] cycloaddition

An asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The corresponding C-1-substituted tetrahydroisoquinoline derivatives were obtained in high yields (>90%) with excellent stereoselectivities (up to 99% ee and >20?:?1 dr). The reaction can be conducted on a gram-scale using a low catalyst loading (0.5 mol%) with high yield and selectivity.

Phosphane-Catalyzed [3+3] Annulation of C,N-Cyclic Azomethine Imines with Ynones: A Practical Method for Tricyclic Dinitrogen-Fused Heterocycles

A phosphane-catalyzed [3+3] annulation of azomethine imines with ynones has been developed. Under mild reaction conditions, the reaction proceeds smoothly to afford tricyclic dinitrogen-fused heterocyclic compounds in moderate to excellent yields with moderate to excellent stereoselectivies. Using a chiral phosphine as the catalyst, the reaction could work to give the cycloadduct in moderate yield with moderate enantioselectivity. (Figure presented.) .

Scaffold Diversity through a Branching Double-Annulation Cascade Strategy: Iminium-Induced One-Pot Synthesis of Diverse Fused Tetrahydroisoquinoline Scaffolds

A branching double-annulation cascade (BDAC) strategy for diverse and complex fused THIQ scaffolds via a highly reactive iminium-induced one-pot double-cyclization sequence involving Pictect-Spengler-type cyclization has been developed for the first time. The salient features of this protocol are that it allows direct and rapid access to unprecedented diverse fused THIQ skeletons, is metal/catalyst free, has a cleaner reaction profile, provides good to excellent yields, and is a convenient approach. This catalyst-free domino process facilitates the double annulation with a variety of scaffold building agents via two C-N and one C-X (X = C, N, O) bond formation in a single step under uniform reaction conditions. Furthermore, we reveal an unusual dual BDAC sequence leading to N-N-linked isoquinoline dimer.

Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinoline and Ethyl (Z)-3-Acetoxy-3-tosylpent-4-enoate through Tertiary-Amine-Catalyzed [3+2] Annulation

The 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed divergent [3+2] annulation of C,N-cyclic azomethine imines with δ-acetoxyallenoates was developed; 5,6-dihydropyrazolo[5,1-a]isoquinolines and ethyl (Z)-3-acetoxy-3-tosylpent-4-enoates were afforded in moderate to good yields in a one-pot manner under mild conditions. This annulation reaction provides a highly efficient method to construct dinitrogen-fused heterocycles and ethyl (Z)-3-acetoxy-3-tosylpent-4-enoates at the same time.

A metal-free cyclic iminium induced one-pot double annulation cascade: Access to dihydroisoquinolinium (DHIQ) salts

A reactive cyclic iminium induced one-pot Groebke-Blackburn-Bienayme (GBB) double annulation cascade (DAC) for the synthesis of skeletally diverse DHIQ salts has been described. The key features of this protocol are transition-metal and solvent-free, mild reaction conditions, robust method, one-step construction of two privileged heterocyclic rings, clean reaction profile and operational simplicity.

A facile one-pot protocol for the synthesis of tetrazolyl-tetrahydroisoquinolines via novel domino intramolecular cyclization/Ugi-azide sequence

A facile one-pot, four-component domino reaction between 2-(2-bromoethyl)benzaldehyde, isocyanide, amine, and azide for the synthesis of tetrazolyl-tetrahydroisoquinoline derivatives has been developed. The reaction sequence involves intramolecular replacement of halide by iminium nitrogen followed by Ugi-azide reaction. The reaction is catalyst/additive free and takes place under ambient conditions with short reaction times to furnish products in good to excellent yields.

A Phosphine-Catalyzed Novel Asymmetric [3+2] Cycloaddition of C,N-Cyclic Azomethine Imines with δ-Substituted Allenoates

Catalytic asymmetric [3+2] cycloadditions of C,N-cyclic azomethine imines with δ-substituted allenoates have been developed in the presence of (S)-Me-f-KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo- and good enantioselectivities under mild condition. The substrate scope has been also examined. This is the first time that δ-substituted allenoates have been applied as a δ,γ-C-C bond participated C 2 synthon in asymmetric synthesis. Another round: Catalytic asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with δ-substituted allenoates have been developed in the presence of (S)-Me-f-KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo- and good enantioselectivities under mild conditions. This is the first example applying δ-substituted allenoates as C 2 synthons in asymmetric δ,γ-C-C bond formation.

In situ generation of nucleophilic allenes by the gold-catalyzed rearrangement of propargylic esters for the highly diastereoselective formation of intermolecular C(sp3)-C(sp2) bonds

New perspectives, in particular for the synthesis of isochromane derivatives (see scheme), are provided by the title reaction. Excellent diastereoselectivites are achieved in this reaction which proceeds through a gold-catalyzed 1,3-acyloxy migration. In some cases exclusively the Z isomer is detected. Copyright