220130-59-6

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 24431-15-0 (E)-N-benzyl-1-(p-tolyl)methanimine 
• 74-90-8 hydrogen cyanide 
• 24431-15-0 N-benzyl-p-tolylmethanimine 
• 104-87-0 4-methyl-benzaldehyde 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

A highly enantioselective Bronsted acid catalyst for the Strecker reaction

(Chemical Equation Presented) An amenable route to amino acids: An optimized new chiral binol phosphate catalyst (see scheme; Ar = 9-phenanthryl) for the hydrocyanation of imines provides a convenient strategy for the enantioselective synthesis of α-amino

Enantioselective Strecker reaction of aldimines using potassium cyanide catalyzed by a recyclable macrocyclic V(v) salen complex

A chiral dimeric macrocyclic V(v) salen complex based on a chiral macrocyclic salen ligand derived from 1R, 2R-(-) diaminocyclohexane with trigol bisaldehyde was synthesized and evaluated as an efficient catalyst (5 mol%) for asymmetric addition of potass

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 R1, R2, R3, and R4 are independently a hydrogen atom, an alkyl group, or the like, and (A) represents a group with two or more carbon atoms. The titanium catalysts may be isolated in solid form and may be stored. The invention further relates to a process for cyanation of imines, wherein the process comprises reacting an imine with a cyanating agent in the presence of the titanium catalyst.

Highly enantioselective titanium-catalyzed cyanation of imines at room temperature

(Figure presented) A highly active and enantioselective titanium-catalyzed cyanatlon of imines at room temperature Is described. The catalyst used Is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields In 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.

Mn(III) salen complexes-catalyzed enantioselective addition of trimethyl silylcyanide to N-benzylimines in the presence of 4-phenyl pyridine-N-oxide as an additive

Chiral monomeric and dimeric Mn(III) salen complexes viz., [(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato manganese(III) chloride and 5,5-methylene di-[(S,S)-{N-(3-tert-butyl salicylidine)-N′-(3′,5′-di-tert-butyl salicylidene)}-1,

Catalytic, asymmetric Strecker reactions catalysed by titaniumIV and vanadiumV(salen) complexes

VanadiumV(salen) complex 3 has been found to be an effective catalyst for the asymmetric addition of hydrogen cyanide (generated in situ from trimethylsilyl cyanide) to imines. The best results (up to 81% enantiomeric excess) were obtained for aromatic imines in which the nitrogen atom is protected with a benzyl group and in which the imine bond is not sterically encumbered.

A highly enantioselective Strecker reaction catalyzed by titanium-N-salicyl-β-aminoalcohol complexes

N-salicyl-β-amino alcohols 1 were synthesized and evaluated as ligands for catalytic asymmetric Strecker reactions. N-Benzhydrylaldimines derived from aromatic and aliphatic aldehydes reacted with TMSCN in the presence of 10 mol% of Ti-1 complex to give t