The scope of a novel alkoxyallene-based pyridine synthesis was expanded to enantiopure carboxylic acids and nitriles as starting materials. The enantiomeric purity of the chiral α-secondary carboxylic acids and nitriles was completely preserved during this reaction sequence thus allowing the one-pot preparation of a whole range of 4-hydroxypyridines or their 4-pyridinone tautomers in good yields.