Functional monomers and polymers, 116. Asymmetric addition of n-butyllithium to aldehydes by chiral polymers and related compounds containing dimethylamino bornanol moieties

Asymmetric addition reaction of n-butyllithium to aldehydes was studied by using chiral polystyrene derivatives and chiral low molecular model compounds, both of which were derived from cis,endo-3-dimethylamino-2-hydroxybornane. The higher optical yields were achieved by using low molecular model compounds, and particularly the highest value was obtained in the case when ether was used as the solvent. The effect of reaction temperature, sort of the solvents and the molar ratio of the reagent to aldehyde on the asymmetric addition was also discussed.