Synthesis and catalytic application of ferrocene substituted camphane-based aminoalcohols and S-containing heterocyclic analogues

Abstract

A facile and practical approach was developed for the synthesis of chiral α-, β-and δ-aminoalcohols and S-containing heterocyclic analogues by using of readily available sources of chirality. The synthetic strategy involves utilization of camphorderived ferrocene-containing starting compounds allowing, by means of nucleophilic additions of functionalized organolithiums, for the preparation of a small library of structurally diverse multifunctional derivatives possessing the bicyclic camphane skeleton as the central core. The new diastereoisomeric pure aminoalcohols and S-containing heterocyclic analogues have been evaluated as precatalysts for the addition of diethyl zinc to benzaldehyde providing in some cases very high enantioselectivity (up to 96%).