1630982-20-5

Upstream product

• 150884-50-7 benzaldehyde N-boc imine 
• 126568-44-3 (S)-3-(N-tert-butoxycarbonylamino)-3-phenylpropanenitrile 
• 765922-42-7 (S)-propyl 3-amino-3-phenylpropanoate 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 614-19-7 (S)-3-amino-3-phenylpropanoic acid 
• 1150560-58-9 methanesulfonic acid (S)-3-tert-butoxycarbonylamino-3-phenylpropyl ester 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 622830-41-5 (+/-)-β-phenylalanine propyl ester 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

A chiral analog of the bicyclic guanidine TBD: Synthesis, structure and Br?nsted base catalysis

Starting from (S)-β-phenylalanine, easily accessible by lipase-catalyzed kinetic resolution, a chiral triamine was assembled by a reductive amination and finally cyclized to form the title compound 10. In the crystals of the guanidinium benzoate salt the six membered rings of 10 adopt conformations close to an envelope with the phenyl substituents in pseudo-axial positions. The unprotonated guanidine 10 catalyzes Diels-Alder reactions of anthrones and maleimides (25-30% ee). It also promotes as a strong Br?nsted base the retro-aldol reaction of some cycloadducts with kinetic resolution of the enantiomers. In three cases, the retroaldol products (48-83% ee) could be recrystallized to high enantiopurity (≥95% ee). The absolute configuration of several compounds is supported by anomalous X-ray diffraction and by chemical correlation.

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).