N-acyldihydropyridones as synthetic intermediates. A stereoselective synthesis of acyclic amino alcohols containing multiple chiral centers.
Various 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. The benzyl bromide can be cleanly reduced, or substituted with various nucleophiles via an S(N)2 process to add additional heteroatoms stereoselectively. This methodology is useful for the stereoselective synthesis of uniquely substituted alkylamine derivatives containing multiple chiral centers and various functionality. Diastereomerically pure amino alcohols containing three to five contiguous stereocenters were prepared using this strategy.
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* / Q000737:chemistry*; D002384:Catalysis; D003488:Cyanogen Bromide / Q000737:chemistry; D006865:Hydrogenation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D008968:Molecular Conformation; D010880:Piperidines / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D000605:Amino Alcohols; D007202:Indicators and Reagents; D010880:Piperidines; D003488:Cyanogen Bromide