Stereoselective Synthesis and Applications of Pinane-Based Chiral 1,4-Amino Alcohol Derivatives

Abstract A new library of pinane-based 1,4-amino alcohols was synthesised and utilised as chiral ligands in enantioselective diethylzinc addition to benzaldehyde. Aldol condensation (+)-nopinone, derived from (–)-β-pinene, with 2-pyridinecarboxaldehyde gave the key intermediate α,β-unsaturated ketone, which transformed diastereoselective reduction, followed by hydrogenation, resulting alcohols. On other hand, epoxidation reduction then hydrogenation pyridine ring, afforded a mixture 4-amino-2,3-epoxy-1-ols. Stereoselective hydride epoxy ketone subsequent products substituted benzyl bromides provided quaternary ammonium salts, were subjected affording 4-amino-2,3-epoxy-1-ol derivatives containing an N-benzylpiperidine moiety. The inhibition nucleophile-initiated opening oxirane ring interpreted systematic series­ comparative Hartree–Fock modelling study using 6-31+G(d,p) basis set. antiproliferative activities 4-amino-2,3-epoxy­-1-ol examined, structure–activity relationships studied aspects stereochemistry saturation, substituent effects on piperidine system.