Medical and Biomedical Researches

Stereoselective Synthesis of Acyclic Amino Alcohols via von Braun Ring Opening of Chiral Piperidines

Stereoselective Synthesis of Acyclic Amino Alcohols via von Braun Ring Opening of Chiral Piperidines.

Multisubstituted piperidines containing a phenyl group at C-2 can be opened regio- and stereoselectively with cyanogen bromide. The ring-opened products contain useful cyanamide and benzylic bromide functional groups. This methodology is useful for the stereoselective synthesis of uniquely substituted alkylamine derivatives containing multiple chiral centers and various functionality.

McCall WS, Grillo TA, Comins DL.