5591-04-8

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

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

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.

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

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