296236-17-4

Upstream product

• 3938-96-3 ethyl 2-methoxyacetate 
• 42070-98-4 1-(p-tolyl)ethylamine 
• 17640-21-0 isopropyl methoxyacetate 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 239105-47-6 (R)-1-(4-methylphenyl)propan-1-amine 

Relevant academic research and scientific papers

Artificial plant cell walls as multi-catalyst systems for enzymatic cooperative asymmetric catalysis in non-aqueous media

The assembly of cellulose-based artificial plant cell wall (APCW) structures that contain different types of catalysts is a powerful strategy for the development of cascade reactions. Here we disclose an APCW catalytic system containing a lipase enzyme and nanopalladium particles that transform a racemic amine into the corresponding enantiomerically pure amide in high yieldviaa dynamic kinetic resolution.

Mesoporous Core-Shell Nanostructures Bridging Metal and Biocatalyst for Highly Efficient Cascade Reactions

Mesoporous core-shell structured nanocatalysts with a PdPt bimetallic core and enzyme-immobilized polydopamine (PDA) shell were designed, in which the PDA shell worked as a barrier to position the bimetallic core and enzyme in separated locations. The accessible mesoporous structures of both the core and shell significantly facilitate mass transfer and catalyst utilization, improving the synergistic catalytic abilities in cascade reactions. The obtained bifunctional nanocatalysts enabled efficient two-step one-pot cascade reactions of different types: dynamic kinetic resolution of primary amines in organic solvent with high yield and enantioselectivity (up to 99% yield and 98% ee) and degradation of organophosphate nerve agent in aqueous solution with high rate constant and turnover frequency number values (0.8 min-1 and 20 min-1, respectively).

Co-immobilization of metal and enzyme into hydrophobic nanopores for highly improved chemoenzymatic asymmetric synthesis

Chemoenzymatic catalysts with hydrophobic nanopores were fabricated by co-immobilizing metal nanoparticles and enzymes into the dendritic organosilica nanoparticles. They demonstrated highly improved catalytic performance in chemoenzymatic asymmetric synthesis of chiral amines and alcohols. The hydrophobic microenvironment proved to be critical to enhanced stability, activity and cascade efficiency. This journal is

Chemoenzymatic Dynamic Kinetic Resolution of Primary Benzylic Amines using Pd0-CalB CLEA as a Biohybrid Catalyst

Herein, we report on the use a biohybrid catalyst consisting of palladium nanoparticles immobilized on cross-linked enzyme aggregates of lipase B of Candida antarctica (CalB CLEA) for the dynamic kinetic resolution (DKR) of benzylic amines. A set of amines were demonstrated to undergo an efficient DKR and the recyclability of the catalysts was studied. Extensive efforts to further elucidate the structure of the catalyst are presented.

Combining Pd nanoparticles on MOFs with cross-linked enzyme aggregates of lipase as powerful chemoenzymatic platform for one-pot dynamic kinetic resolution of amines

Acquisition of chiral amines is a very important item in scientific research. Chemoenzymatic catalyst combination of Pd nanoparticles supported on the external surface of the ethylenediamine-functionalized MIL-101 (Pd?ED-MIL-101) with layered cross-linked

Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis

Organic synthesis is in general performed using stepwise transformations where isolation and purification of key intermediates is often required prior to further reactions. Herein we disclose the concept of integrated heterogeneous metal/enzymatic multiple relay catalysis for eco-friendly and asymmetric synthesis of valuable molecules (e.g., amines and amides) in one-pot using a combination of heterogeneous metal and enzyme catalysts. Here reagents, catalysts, and different conditions can be introduced throughout the one-pot procedure involving multistep catalytic tandem operations. Several novel cocatalytic relay sequences (reductive amination/amidation, aerobic oxidation/reductive amination/amidation, reductive amination/kinetic resolution and reductive amination/dynamic kinetic resolution) were developed. They were next applied to the direct synthesis of various biologically and optically active amines or amides in one-pot from simple aldehydes, ketones, or alcohols, respectively.

SYNTHESIS OF AMIDES AND AMINES FROM ALDEHYDES OR KETONES BY HETEROGENEOUS METAL CATALYSIS

This invention concerns the first mild and efficient synthesis of primary amines and amides from aldehydes or ketones using a heterogeneous metal catalystand amine donor. The initial heterogeneous metal- catalyzed reaction between the carbonyl and the amine donor components is followed up with the addition of a suitable acylating agent component in one-pot. Hence, the present invention provides a novel catalytic one-pot three-component synthesis of amides. Moreover, the integration of enzyme catalysis allows for eco-friendly one-pot co-catalytic synthesis ofamides from aldehyde and ketone substrates, respectively. The process can be applied to the co-catalytic one-pot three-component synthesis of capsaicin and its analogues from vanillin or vanillyl alcohol. It can also be applied for asymmetric synthesis. In the present invention, a novel co-catalytic reductive amination/dynamic kinetic resolution (dkr) relay sequence for the asymmetric synthesis of optically active amides from ketones is disclosed. Moreover, implementation of a catalytic reductive amination/kinetic resolution (kr) relay sequence produces the corresponding optically active amide product and optical active primary amine product with the opposite stereochemistry from the starting ketones.

Chemoenzymatic dynamic kinetic resolution of primary amines using a recyclable palladium nanoparticle catalyst together with lipases

A catalyst consisting of palladium nanoparticles supported on amino-functionalized siliceous mesocellular foam (Pd-AmP-MCF) was used in chemoenzymatic dynamic kinetic resolution (DKR) to convert primary amines to amides in high yields and excellent ee's.

Solvent-free kinetic resolution of primary amines catalyzed by Candida antarctica lipase B: Effect of immobilization and recycling stability

Highly enantioselective (E >200) N-acylation of nine racemic primary amines with isopropyl methoxyacetate in the presence of Candida antarctica lipase B (Novozym 435) has been reported to yield the unreacted (S)-amines (ee ≥98%) and produced the (R)-amides (ee ≥95%) at 50% conversion under solvent-free conditions. One of the amines and the acyl donor have been used in an equimolar ratio at room temperature (23 °C). Under the reaction conditions, the reuse stability of Novozym 435 with 1-phenylethylamine (as a model compound) has been shown to be poor while somewhat improved stability has been observed with an in-house prepared sol-gel CAL-B catalyst.

Fast racemization and dynamic kinetic resolution of primary benzyl amines

We prepared a Pd nanocatalyst (average diameter of Pd nanoparticles = 1.73 nm) displaying a remarkable activity for the racemization and dynamic kinetic resolution (DKR) of 1-methylbenzylamine. It was eight times more active than the previous best. The DKR of 1-methylbenzylamine with the Pd nanocatalyst (2 mol %) in the presence of a thermostable lipase (Novozym 435) was complete in 6 h at 70 °C. The DKRs of other benzyl amines also proceeded to completion in 6 h under similar conditions except the amount of Pd nanocatalyst.