6907-71-7

Upstream product

• 98-86-2 acetophenone 
• 74-89-5 methylamine 
• 920-68-3 heptamethyldisilazane 
• 40347-03-3 dimethylaluminium-(N-methyl-trimethylsilyl)amide 
• 32366-26-0 cumyl azide 
• 97325-80-9 1-Benzyl-4,5-dimethyl-5-phenyl-4,5-dihydro-1H-tetrazole 
• 118762-10-0 N-chloro-N,α-dimethylbenzylamine 
• 118761-68-5 C₉H₁₂BrN 
• 51041-97-5 N-methyl-N-trimethylsilylcarbamic acid trimethylsilyl ester 
• 100-42-5 styrene 
• 19131-99-8 N-methyl-N-[(S)-1-phenylethyl]amine 
• 5933-40-4 (R)-(+)-N,α-dimethylbenzylamine 
• 42882-26-8 N-methyl-N-(1-phenylethyl)amine 

Downstream Products

• 77130-13-3 N-Methylthiophenylacetamide 
• 37760-43-3 4,5-dimethyl-3,5-diphenyl-4,5-dihydro-[1,2,4]oxadiazole 
• 148564-74-3 N-(α-methylenebenzyl)-N-methoxalylmethylamine 
• 142609-28-7 2,2-dichloro-N-methyl-N-(1-phenylvinyl)acetamide 
• 61820-45-9 Methyl-(1-phenyl-vinyl)-trimethylsilanyl-amine 
• 1826-12-6 4-phenyl-thiazole 
• 19367-22-7 (1RS,3SR)-3-methylamino-1,3-diphenyl-propan-1-ol 
• 19367-22-7 (1RS,3RS)-3-methylamino-1,3-diphenyl-propan-1-ol 
• 105909-74-8 1-methyl-6-phenyl-3,4-dihydro-1H-pyridin-2-one 
• 90788-47-9 1-methyl-2-phenyl-Δ²-pyrroline-4,5-dione 

Relevant academic research and scientific papers

Deactivation mechanisms of iodo-iridium catalysts in chiral amine racemization

The homogenous, [IrCp?I2]2, SCRAM catalyst (1) is active in the racemization of chiral amines. NMR, kinetic and structural mechanistic studies have determined the cause of catalyst deactivation to occur when ammonia or methylamine are liberated by hydrolysis or aminolysis of the intermediate imine, which tightly coordinate to the iridium centre to block turnover. Control of moisture and substrate concentration can suppress deactivation, whilst partial reactivation of spent catalyst was identified using hydroiodic acid.

Continuous Flow Chiral Amine Racemization Applied to Continuously Recirculating Dynamic Diastereomeric Crystallizations

A new, dynamic diastereomeric crystallization method has been developed, in which the mother liquors are continuously separated, racemized over a fixed-bed catalyst, and recirculated to the crystallizer in a resolution-racemization-recycle (R3) process. S

CHIRALITY SENSING WITH MOLECULAR CLICK CHEMISTRY PROBES

The present invention relates to an analytical method that includes providing a sample potentially containing a chiral analyte that can exist in stereoisomeric forms, and providing a probe selected from the group consisting of coumarin-derived Michael acceptors, dinitrofluoroarenes and analogs thereof, arylsulfonyl chlorides and analogs thereof, arylchlorophosphines and analogs thereof, aryl halophosphites, and halodiazaphosphites. The sample is contacted with the probe under conditions to permit covalent binding of the probe to the analyte, if present in the sample; and, based on any binding that occurs, the absolute configuration of the analyte in the sample, and/or the concentration of the analyte in the sample, and/or the enantiomeric composition of the analyte in the sample is/are determined. The probe may be a coumarin-derived Michael acceptor, a di nitrofluoroarene or analog thereof, an arylsulfonyl chloride or analog thereof, an arylchlorophosphine or analog thereof, an aryl halophosphite, or a halodiazaphosphite.

Photocatalytic Difunctionalization of Vinyl Ureas by Radical Addition Polar Truce–Smiles Rearrangement Cascades

We report tandem alkyl-arylations and phosphonyl-arylations of vinyl ureas by way of a photocatalytic radical-polar crossover mechanism. Addition of photoredox-generated radicals to the alkene forms a new C?C or C?P bond and generates a product radical adjacent to the urea function. Reductive termination of the photocatalytic cycle generates an anion that undergoes a polar Truce–Smiles rearrangement, forming a C?C bond. The reaction is successful with a range of α-fluorinated alkyl sodium sulfinate salts and diarylphosphine oxides as radical precursors, and the conformationally accelerated Truce–Smiles rearrangement is not restricted by the electronic nature of the migrating aromatic ring. Formally the reaction constitutes an α,β-difuctionalisation of a carbon–carbon double bond, and proceeds under mild conditions with visible light and a readily available organic photocatalyst. The products are α,α-diaryl alkylureas typically functionalized with F or P substituents that may be readily converted into α,α-diaryl alkylamines.

Tackling N-Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron-Catalyzed Synthesis of α-Chiral Amines

A readily activated iron alkyl precatalyst effectively catalyzes the highly enantioselective hydroboration of N-alkyl imines. Employing a chiral bis(oxazolinylmethylidene)isoindoline pincer ligand, the asymmetric reduction of various acyclic N-alkyl imines provided the corresponding α-chiral amines in excellent yields and with up to >99 % ee. The applicability of this base metal catalytic system was further demonstrated with the synthesis of the pharmaceuticals Fendiline and Tecalcet.

Cooperative Lewis Acid/Cp?CoIII Catalyzed C-H Bond Activation for the Synthesis of Isoquinolin-3-ones

A facile route toward the synthesis of isoquinolin-3-ones through a cooperative B(C6F5)3- and Cp?CoIII-catalyzed C-H bond activation of imines with diazo compounds is presented. The inclusion of a catalytic amount of B(C6F5)3 results in a highly efficient reaction, thus enabling unstable NH imines to serve as substrates. CoIII-operative catalysis: The first facile route toward the synthesis of isoquinolin-3-ones through cooperative C-H bond activation with B(C6F5)3 (BCF in picture) and Cp?CoIII (Cp?=C5Me5) is presented. The newly developed catalytic system is highly reactive, thus unstable NH imines can serve as substrates.

Characterization of three novel enzymes with imine reductase activity

Imine reductases (IRED) are promising catalysts for the synthesis of optically pure secondary cyclic amines. Three novel IREDs from Paenibacillus elgii B69, Streptomyces ipomoeae 91-03 and Pseudomonas putida KT2440 were identified by amino acid or structural similarity search, cloned and recombinantly expressed in E. coli and their substrate scope was investigated. Besides the acceptance of cyclic amines, also acyclic amines could be identified as substrates for all IREDs. For the IRED from P. putida, a crystal structure (PDB-code 3L6D) is available in the database, but the function of the protein was not investigated so far. This enzyme showed the highest apparent E-value of approximately Eapp = 52 for (R)-methylpyrrolidine of the IREDs investigated in this study. Thus, an excellent enantiomeric purity of >99% and 97% conversion was reached in a biocatalytic reaction using resting cells after 24 h. Interestingly, a histidine residue could be confirmed as a catalytic residue by mutagenesis, but the residue is placed one turn aside compared to the formally known position of the catalytic Asp187 of Streptomyces kanamyceticus IRED.

Iron catalysed nitrosation of olefins to oximes

Fe(BF4)2·6H2O/2,6- pyridinedicarboxylic acid catalysed nitrosation of a wide variety of substituted styrenes has been developed in the presence of t-BuONO/NaBH4 under H2 pressure (10 bar) in MeOH-H2O (5 : 1) to afford corresponding oximes in good to excellent yields.

Amines bearing tertiary substituents by tandem enantioselective carbolithiation-rearrangement of vinylureas

In the presence of (-)-sparteine or a (+)-sparteine surrogate, organolithiums add to N-alkenyl-N'-arylureas to give benzylic organolithiums in an enantioselective manner. Under the influence of DMPU, these organolithiums undergo rearrangement with migrati

Geometry-selective synthesis of e or Z N -vinyl ureas (N -carbamoyl enamines)

N-Vinyl ureas are emerging as a valuable class of compounds with both nucleophilic and electrophilic reactivity. They may be made by capturing the enamine tautomer of an imine with an isocyanate, a reaction which in general leads to the E isomer of the vi