Stereoselective Synthesis of Acyclic Amino Alcohols via von Braun Ring Opening of Chiral Piperidines
journal contributionposted on 2008-08-07, 00:00 authored by W. Stephen McCall, Teresa Abad Grillo, Daniel L. Comins
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.