Reduction of N-Acyl-2,3-dihydro-4-pyridones to N-Acyl-4-piperidones Using Zinc/Acetic Acid
Daniel L. Comins, Clinton A. Brooks and Charles L. Ingalls
*Department of Chemistry, North Carolina State University,
Raleigh, North Carolina 27695-8204, USA,
Email: dlcomins
ncsu.edu
D. L. Comins, C. A. Brooks, C. L. Ingalls, J. Org. Chem., 2001, 66, 2181-2182.
DOI: 10.1021/jo001609l
Abstract
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.
see article for more examples
chemoselectivity
Key Words
2,3-dihydro-4-pyridones, 4-piperidones, Zinc, 1,4-reduction, reduction of enamines
ID: J42-Y2001
