159848-75-6

Upstream product

• 7605-28-9 2-(phenylsulfonyl)acetonitrile 
• 479423-40-0 N-tert-butyl 4-methoxybenzylidenecarbamate 
• 32083-60-6 2-(naphthalene-2-ylsulfonyl)acetonitrile 
• 193073-85-7 methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)acetate 
• 159848-74-5 1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate 
• 151-50-8 potassium cyanide 
• 159990-11-1 (R)-2-tert-butoxycarbonylamino-1-methanesulfonyloxy-2-(4-methoxyphenyl)ethane 

Downstream Products

• 1630982-21-6 C₁₅H₂₄N₂O₃ 
• 159848-85-8 (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-97-2 (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-87-0 (3S,3'S)-3-<3'-acetoxy-N-tert-butoxycarbonyl-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-95-0 methyl (3S,3S')-3--3-(4-methoxyphenyl)propionate 
• 159848-86-9 (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-83-6 methyl (3S,3'S)-3--3-(4-methoxyphenyl)propionate 
• 159848-96-1 (3S,3S')-3--3-(4-methoxyphenyl)-1-propanol 
• 159848-84-7 [(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-phenyl)-propyl]-[(S)-3-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester 
• 159848-94-9 methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate 
• 159848-82-5 methyl (3S,3'S)-3-<3'-tert-butyldimethylsiloxy-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate 
• 96363-21-2 methyl (S)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionate 
• 159990-12-2 (S)-3-tert-Butoxycarbonylamino-3-(4-methoxy-phenyl)-propionic acid 
• 159848-76-7 methyl (+)-(3S)-3-amino-3-(4-methoxyphenyl)propanoate 

Relevant academic research and scientific papers

Ureidopeptide-based Bronsted bases: Design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles

The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Bronsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis. Learning from peptides: A concise route for the catalytic enantioselective synthesis of β-amino nitriles has been achieved by using ureidopeptide-based Bronsted bases as catalysts in the Mannich reaction of N-Boc imines and (arylsulfonyl)acetonitriles (see scheme; Boc=tert-butoxycarbonyl, napht=naphthyl, TMS=trimethylsilyl).

Catalytic enantioselective mannich-type reaction with β-phenyl sulfonyl acetonitrile

Figure presented The organocatalytic addition of β-phenyl sulfonyl acetonitrile 1 to either N-Boc-protected α-amido sulfones or imines allowed the synthesis of enantioenriched α-unsubstituted β-amino nitriles through a Mannich-type reaction.

Total Synthesis of 2'-Deoxymugineic Acid and Nicotianamine

Steroselective total synthesis of the unique phytosiderophores, 2'-deoxymugineic acid (4) and nicotianamine (5), has been achieved from the β-tyrosine derivative 21 using its aryl groups as the carboxyl synthon.