Stereoselective synthesis of 2,5,6-trisubstituted piperidines.
[reaction: see text] A short and efficient synthesis of 2,5,6-trisubstituted piperidines was achieved by a combination of an aza-Achmatowicz oxidation of a furyl benzenesulfonamide, conjugate addition to the resulting 2H-pyridinone, and subsequent addition of various nucleophiles to a transient N-sulfonyliminium ion. The steric bulk of the tosyl group directs attack of the nucleophile from its opposite side, thereby leading to the formation of cis-substituted products.
Harris
Joel M
JM
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Padwa
Albert
A
D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry
D010880:Piperidines