Categories: Synthesis of N-Heterocycles > Synthesis of Cyclic Amines >
Synthesis of 4-piperidones
Recent Literature
Conjugate reduction of dihydropyridones have generally been carried out using
expensive L or K-Selectrides, as catalytic hydrogenation often leads to over
reduction. The use of zinc/acetic acid enables a simple, inexpensive, and mild
reduction of N-acyl-2,3-dihydro-4-pyridones to various racemic or
enantiopure 4-piperidones or indolizidinones.
D. L. Comins, C. A. Brooks, C. L. Ingalls, J. Org. Chem., 2001,
66, 2181-2182.
A highly enantioselective, catalytic three-component coupling of aldehydes,
alkynes, and 4-piperidone hydrochloride hydrate affords the corresponding
tertiary propargylamines in useful yields. A selective cleavage of the
piperidone protecting group is possible using either ammonia/EtOH or a
polymer-supported scavenger amine.
P. Aschwanden, C. R. J. Stephenson, E. M. Carreira, Org. Lett.,
2006,
8, 2437-2440.