Synthesis of 1,3-amino alcohol derivatives via a silicon-mediated ring-opening of substituted piperidines.
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.
McCall
W Stephen
WS
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
Comins
Daniel L
DL
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*
D000605:Amino Alcohols; D010880:Piperidines; D014297:Trimethylsilyl Compounds; D003488:Cyanogen Bromide