title: Stereoselective synthesis of acyclic amino alcohols via von Braun ring opening of chiral piperidines.
abstract: 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.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
authors.forename: W Stephen
authors.initials: WS
authors.lastname: McCall
authors.forename: Teresa Abad
authors.initials: TA
authors.lastname: Grillo
authors.forename: Daniel L
authors.initials: DL
authors.lastname: Comins
mesh_terms: 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
chemical_list: D000605:Amino Alcohols; D001593:Benzyl Compounds; D010880:Piperidines; D003484:Cyanamide; D003488:Cyanogen Bromide; C038682:benzyl bromide