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
W Stephen
WS
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
Grillo
Teresa Abad
TA
Comins
Daniel L
DL
D000605:Amino Alcohols / Q000138:chemical synthesis*; D001593:Benzyl Compounds / Q000737:chemistry; D003484:Cyanamide / Q000737:chemistry; D003488:Cyanogen Bromide / Q000737:chemistry; D003500:Cyclization; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism
D000605:Amino Alcohols; D001593:Benzyl Compounds; D010880:Piperidines; D003484:Cyanamide; D003488:Cyanogen Bromide; C038682:benzyl bromide