Synthesis of 1,3-Amino Alcohol Derivatives via a Silicon-Mediated Ring-Opening of Substituted Piperidines

Abstract

Multisubstituted piperidines containing a trimethylsilylmethyl group at C-2 can be opened regioselectively with TBAF and cyanogen bromide. The ring-opened products contain synthetically useful cyanamide and terminal alkene functional groups. This method is useful for the stereoselective synthesis of alkylamine derivatives containing multiple chiral centers.