61806-77-7

Upstream product

• 143063-61-0 2-hexanone N-benzyl imine 
• 591-78-6 n-hexan-2-one 
• 932-90-1 Benzaldoxime 
• 693-03-8 n-butyl magnesium bromide 
• 588-46-5 N-(phenylmethyl)acetamide 
• 100-46-9 benzylamine 

Downstream Products

• 70492-67-0 (S)-hexan-2-amine 
• 5329-79-3 (R)‐2‐aminohexane 

Relevant academic research and scientific papers

A Mechanism for Reductive Amination Catalyzed by Fungal Reductive Aminases

Reductive aminases (RedAms) catalyze the asymmetric reductive amination of ketones with primary amines to give secondary amine products. RedAms have great potential for the synthesis of bioactive chiral amines; however, insights into their mechanism are currently limited. Comparative studies on reductive amination of cyclohexanone with allylamine in the presence of RedAms, imine reductases (IREDs), or NaBH3CN support the distinctive activity of RedAms in catalyzing both imine formation and reduction in the reaction. Structures of AtRedAm from Aspergillus terreus, in complex with NADPH and ketone and amine substrates, along with kinetic analysis of active-site mutants, reveal modes of substrate binding, the basis for the specificity of RedAms for reduction of imines over ketones, and the importance of domain flexibility in bringing the reactive participants together for the reaction. This information is used to propose a mechanism for their action and also to expand the substrate specificity of RedAms using protein engineering.

Simple Metal-Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

This work describes the use of cheap, safe, and easy-to-handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal-free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability. (Figure presented.).

Direct transformation of secondary amides into secondary amines: Triflic anhydride activated reductive alkylation

Versatile and mild: The first general method for the title transformation has been developed (see scheme; 2-F-Py=2-fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the r

Reductive amination of aldehydes and ketones with primary amines by using lithium amidoborane as reducing reagent

A variety of secondary amines were obtained in high isolated yields in the reductive amination of aldehydes and ketones by using lithium amidoborane as reducing agent. Compared to ammonia borane, lithium amidoborane has higher reducibility, and thus, exhibits faster reaction rate.

Hydroamination of carbonyl compounds with oximes

N-alkyl(cycloalkyl)benzylamines, p-fluorobenzylamines, (1-phenylethyl) amines, [1-(p-fluorophenyl)ethyl]amines were synthesized by hydroamination of aldehydes and ketones with oximes.

The hydrosilylation of aid- and ketimines catalyzed by titanocene complexes

Different titanocene complexes 1-10 were tested in the catalytic hydrosilylation of ald- and ketimines with Ph2SiH2. The highest conversions were obtained with Cp2Ti(PhC≡CSiMe3) 1 up to 98% at room temperature.

Catalytic asymmetric and non-asymmetric reduction of times and oximes using metal catalysts

A process is provided for catalytically reducing imines, oximes, hydrazones and related compounds. Moreover, there is provided a process for the catalytic asymmetric reduction of imines, oximes, hydrazones, and the like, using enantiomerically enriched catalysts, to provide chiral amine reaction products which are enriched in one enantiomer. Catalytic asymmetric reduction can also be carried out using an achiral precatalyst in combination with a The U.S. Government has rights in this invention pursuant to NIH Grant Number GM 34917.