A General Synthetic Route to Optically Active Alkylpyridines from Alkylsubstituted Succinaldehyde Monoacetals

Abstract

Succinaldehyde monoacetals (I), a class of organic compounds accessible through hydroformylation of α, β-unsaturated aldehyde acetals using rhodium catalysts¹, are very useful intermediates in several organic syntheses.^1,2 On searching for more simple and efficient synthetic methods for obtaining consistent amounts of optically active mono- and dialkylpyridines (IV), we have investigated the homologation of compounds I to the corresponding glutaraldehyde monoacetals (II) and related 1,5-dioxo compounds or their precursors, which are the most usual starting products for preparing pyridine derivatives.^3,4,5