187819-60-9

Upstream product

• 2179-92-2 tri-n-butyltin cyanide 
• 100-52-7 benzaldehyde 
• 91-00-9 Benzhydrylamine 
• 151-50-8 potassium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 62506-88-1 N-benzylidenediphenylmethanamine 
• 631-57-2 Acetyl cyanide 
• 74-90-8 hydrogen cyanide 
• 62506-88-1 (E)-N-(phenylmethylene)benzhydrylamine 

Downstream Products

• 54295-56-6 2-(benzhydrylamino)-1,2-diphenylethanol 
• 54295-56-6 2-(benzhydrylamino)-1,2-diphenylethanol 

Relevant academic research and scientific papers

Investigation of diketopiperazines containing a guanidino-functionalized sidechain as potential catalysts of enantioselective strecker reactions

Diketopiperazine 1 consisting of L-(γ-guanidino-α-amino) butyric acid and L-phenylalanine was synthesized as the hydroacetate and as the hydronitrate. Its structure was confirmed by X-ray analysis. In contrast to reports in the litera ture (Lipton et al.)

Facile Synthesis of α-Amino Nitrites Using Lanthanide Triflate as a Lewis Acid Catalyst

In the presence of a catalytic amount of lanthanide inflate, imines reacted with cyanotrimethylsilane (TMSCN) to afford α-amino nitriles in excellent yields. Although some imines are difficult to prepare and purify, three-component reactions of aldehydes,

Highly Active Chiral Dilithium(I) Binaphthyldisulfonate Catalysts for Enantio- And Chemoselective Strecker-Type Reactions

An enantioselective Strecker-type reaction of aldimines and ketimines was developed by using a chiral dilithium(I) binaphthyldisulfonate as a chiral acid-base cooperative catalyst. The present catalytic system features an extremely short reaction time (10 min to 4 h), unlike conventional catalytic systems. Along with the design of stronger chiral Li(I) Lewis acid catalysts, a highly reactive pentacoordinate silicate generated in situ could promote the reactions. In particular, instead of unstable N-Bn Strecker products, more stable N-CH2(9-anthryl) and N-CH2(1-naphthyl) Strecker products could be obtained in high yields with high enantioselectivities. By a switch of the present and previous catalyst systems, chemoselective cyanation to a ketoaldimine could be performed, respectively. Moreover, mechanistic investigations provided useful information regarding the active catalysts, catalytic cycles, and possible transition states.

Three helical chain-based 3D coordination polymers: Solvent-induced syntheses, tunable structures and catalytic properties for the Strecker reaction

Three three-dimensional (3D) helical chain-based coordination polymers [Sc(aip)(OH)·(H2O)]n (1), [Sc2(aip)3]n (2) and [Sc2(nip)3]n (3) (H2aip = 5-aminoisoph

In(III) and Sc(III) based coordination polymers derived from rigid benzimidazole-5,6-dicarboxylic acid: Synthesis, crystal structure and catalytic property

Two new coordination polymers (CPs), [InCl(H2bidc)2(H2O)]n (1) and [Sc(Hbidc)(OH)(H2O)]n (2) (H3bidc = benzimidazole-5,6-dicarboxylic acid) were synthesized through a solvotherma

An in-based 3D metal-organic framework as heterogeneous Lewis acid catalyst for multi-component Strecker reactions

A novel three-dimensional metal-organic framework (MOF) {[In3(NIPH)3 (HNIPH)(OH)2]·4H2O}n (1) (H2NIPH = 5-nitroisophthalic acid) with one-dimensional channels was synthesized and structurally characterized. Importantly, it demonstrates excellent catalytic activity for the Strecker reactions of two or three components under mild conditions. Moreover, the catalytic recycling of 1 as a representative example was explored. It can be easily separated and reused for no less than five runs with more than 80% conversion yield in catalytic ability.

Highly Stereoselective Strecker Synthesis Induced by a Slight Modification of Benzhydrylamine from Achiral to Chiral

2-Methylbenzhydrylamine is a chiral variant of achiral benzhydrylamine; however, the chirality formed from the small difference between the phenyl and o-tolyl groups is not expected to induce sufficient stereoselectivity in conventional homogeneous reactions. Initiated by the spontaneous formation and asymmetric amplification of the enantioenriched N-benzhydryl-α-aminonitrile forming conglomerate, we here report that (S)- and (R)-configured title amine, upon the Strecker reaction with achiral aldehydes and HCN, afford the corresponding α-aminonitriles with up to >99.5 % diastereomeric excess, in conjunction with an enhancement of chirality in the solid state. l-Alanine with 98 % ee was synthesized from the (S)-amine by using the method discussed here. Achiral aromatic and heteroaromatic aldehydes could also be successfully utilized to afford chiral α-aminonitriles in a highly stereoselective manner. The stereodivergent synthesis of styrylglycine nitriles has also been accomplished by using racemic and enantioenriched 2-methylbenzhydrylamine. Thus, accompanied with a small rearrangement of the common substrate from achiral toward chiral, the present reactions induce an enhancement of chirality, and expands the concept of stereoselective synthesis to increase the opportunity to access highly enantioenriched compounds such as α-amino acids.

Self-supported chiral titanium cluster (SCTC) as a robust catalyst for the asymmetric cyanation of imines under batch and continuous flow at room temperature

A robust heterogeneous self-supported chiral titanium cluster (SCTC) catalyst and its application in the enantioselective imine-cyanation/Strecker reaction is described under batch and continuous processes. One of the major hurdles in the asymmetric Strecker reaction is the lack of availability of efficient and reusable heterogeneous catalysts that work at room temperature. We exploited the readily hydrolyzable nature of titanium alkoxide to synthesize a self-supported chiral titanium cluster (SCTC) catalyst by the controlled hydrolysis of a preformed chiral titanium-alkoxide complex. The isolated SCTC catalysts were remarkably stable and showed up to 98% enantioselectivity (ee) with complete conversion of the imine within 2 h for a wide variety of imines at room temperature. The heterogeneous catalysts were recyclable more than 10 times without any loss in activity or selectivity. The robustness, high performance, and recyclability of the catalyst enabled it to be used in a packed-bed reactor to carry out the cyanation under continuous flow. Up to 97% ee and quantitative conversion with a throughput of 45 mgh-1 were achieved under optimized flow conditions at room temperature in the case of benzhydryl imine. Furthermore, a three-component Strecker reaction was performed under continuous flow by using the corresponding aldehydes and amines instead of the preformed imines. A good product distribution was obtained for the formation of amino nitriles with ee values of up to 98%. Synthetically useful ee values were also obtained for challenging α-branched aliphatic aldehyde by using the three-component continuous Strecker reaction.

TITANIUM COMPOUNDS AND PROCESS FOR CYANATION OF IMINES

The present invention relates to titanium catalysts for synthesis reactions produced by bringing a reaction mixture comprising a titanium alkoxide and a ligand in contact with water, wherein the ligand is represented by the general formula (e): wherein R

Asymmetrie three-component strecker reactions catalyzed by trans-4-hydroxy-L-proline-derived N,N′-dioxides

Novel trans-4-hydroxy-L-proline-derived N,N′-dioxides have been developed and used as efficient organocatalysts for the one-pot three-component Strecker reaction with an aldehyde, (1,1-diphenyl)methylamine, and TMSCN. Both aromatic and aliphatic aldehydes