SYNTHESIS AND APPLICATION OF NEW BETA-AMINO ALCOHOLS BASED ON THE OCTAHYDRO-CYCLOPENTA[B]PYRROLE SYSTEM IN THE CATALYTIC ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE

Starting from an industrial waste material, the synthesis of a series of new, artificial beta-amino alcohol structures (all-R)-6-10 and 13-1 6 based on the octahydrocyclopenta[b]pyrrole system is presented. Thes e structures were also the subject of studies aimed at developing effe ctive catalysts for enantioselective alkylation by diethylzinc. Attent ion was focussed on stereochemical and steric aspects of the catalyst (-precursor) structure. Potent chiral ligands have been developed reac hing excellent enantioselectivities, e.g. op-values up to 99% with pre dominant formation of the (R)-configurated alkylation products. (C) 19 97 Elsevier Science Ltd.