title: 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.
authors: Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
authors: W Stephen
authors: WS
authors: McCall
authors: Daniel L
authors: DL
authors: Comins
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D003488:Cyanogen Bromide / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000605:Amino Alcohols; D010880:Piperidines; D014297:Trimethylsilyl Compounds; D003488:Cyanogen Bromide