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Synthesis of 4-piperidones

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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.