5537-49-5

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 143-33-9 sodium cyanide 
• 100-42-5 styrene 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 100-47-0 benzonitrile 
• 5581-84-0 3-amino-3-phenylpropanenitrile 
• 98-59-9 p-toluenesulfonyl chloride 
• 1823-99-0 3-amino-3-phenylacrylonitrile 
• 127-65-1 chloroamine-T 
• 151-50-8 potassium cyanide 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 

Downstream Products

• 155496-06-3 (+/-)-3-phenyl-3-(toluene-4-sulfonylamino)-propionic acid 
• 86900-31-4 (+/-)-3-phenyl-3-(toluene-4-sulfonylamino)-propionamide 

Relevant academic research and scientific papers

An efficient method for opening N -tosylaziridines with silylated nucleophiles by using polystyrene-supported 1,5,7-triazabicyclo[44.0]dec-5-ene as a reusable organocatalyst

Polystyrene-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PS-TBD) catalyzes the ring opening of N-tosylaziridines with trimethylsilyl cyanide, trimethylsilyl azide, or trimethylsilyl halides to give the corresponding products in high yields. PS-TBD can b

Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated nucleophiles

Polystyrene-supported TBD (PS-TBD) catalyzes the ring-opening of N-tosylaziridines with silylated nucleophiles to give the corresponding products in high yields. PS-TBD was easily recovered and reused without significant loss of catalytic activity.

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

Organocatalytic trifluoromethylation of imines using phase-transfer catalysis with phenoxides. A general platform for catalytic additions of organosilanes to imines

A new approach to additions of silicon nucleophiles to imines was developed. The method is based on the phase-transfer of phenoxides by ammonium catalysts, overcoming the inability of amide adducts in promoting the reactions.

TTMPP: An efficient organocatalyst in the ring-opening of aziridines with silylated nucleophiles

The ring-opening of N-tosylaziridines with silylated nucleophiles catalyzed by tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) afforded the corresponding β-functionalized sulfonamides in excellent yield under mild reaction conditions.

Ring opening and expansion of aziridines in a silica-water reaction medium

Ring-opening reactions of N-tosylaziridines with water-soluble nucleophiles proceeded in a silica-water reaction medium. The system is applicable to a ring expansion of an aziridine with potassium thiocyanate, leading to a thiazolidine derivative.

Lewis base catalyzed ring opening of aziridines with silylated nucleophiles

(Chemical Equation Presented) The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N′,N′- tetramethylethylenediamine, led to the production of β-functionalized sulfonamides in good to excellent yields with high regi

Synthesis and microbial transformation of β-amino nitriles

Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce β-amino amides and acids from β-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitriles gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work.

Opening of N-Tosyl Aziridines with Nucleophiles Catalyzed by Phosphomolybdic Acid Supported on Silica Gel

An environmentally benign H3PMo12O40-SiO2-catalyzed regioselective opening of activated aziridines with alcohols, azide, cyanide and bromide, at ambient temperature to afford the corresponding β-amino derivatives in good yields is described.

Do aziridines require Lewis acids for cleavage with ionic nucleophiles?

A variety of activated aziridines were cleaved by sodium azide and sodium cyanide in aqueous acetonitrile at reflux, in the absence of any Lewis acid, to provide ring-opened products in quantitative yields. However, the reaction was sluggish in the ring o