1240591-16-5

Upstream product

• 5581-84-0 3-amino-3-phenylpropanenitrile 
• 98837-46-8 P,P-diphenyl-N-(phenylmethylene)phosphinic amide 
• 58156-56-2 N-benzylidene-diphenylthiophosphinamide 
• 100-47-0 benzonitrile 
• 1823-99-0 3-amino-3-phenylacrylonitrile 

Relevant academic research and scientific papers

Direct catalytic asymmetric addition of acetonitrile to N-thiophosphinoylimines

Direct catalytic addition of acetonitrile pronucleophiles to thiophosphinoylimines is described. Soft Lewis acid-hard Bronsted base cooperative catalysis is crucial to promote this elusive carbon-carbon bond-forming reaction in an enantioselective fashion

Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium

A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3-hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo-aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β-aminonitriles, structural analogues of β-hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α- aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation.

Direct Catalytic Asymmetric Addition of Acetonitrile to Aldimines

Despite significant advances in catalytic asymmetric reactions with decent stereocontrol, those using acetonitrile as a pronucleophile are often disregarded due to their low reactivity and insufficient enantioselectivity. Herein we report the resurgence of this reaction in the chemical toolbox with high enantioselectivity (avg. > 95% ee). The combined use of a Ni(II) complex ligated with a chiral biscarbene and tBuOK engages acetonitrile in the catalytic generation of an α-cyanocarbanion and subsequent highly enantioselective addition to aldimines.

Catalytic enantioselective decarboxylative cyanoalkylation of imines by using palladium pincer complexes with C2-symmetric chiral Bis(imidazoline)s

Manifold products: The enantioselective decarboxylative Mannich-type reaction of cyanoacetic acid with N- (2-pyridinesulfonyl)imines catalyzed by chiral 1,3-bis(imidazolin-2-yl)benzene (Phebim)-PdII complexes afforded products with good enantioselectivity (see scheme). The reaction was applied to a wide range of imines with good yield and enantioselectivity. The obtained products can be converted into various compounds without the loss of enantiopurity. Copyright

Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870

A range of β-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the co