Ureidopeptide- Based Bronsted Bases: Design, Synthesis and Application to the Catalytic Enantioselective Synthesis of b- Amino Nitriles from ( Arylsulfonyl) acetonitriles

The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of -amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of -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 -amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis.