Synthesis of chiral ferrocenyl aminoalcohols involving a diastereospecific oxidation: Use in asymmetric catalysis

Abstract

The synthesis of six new chiral ferrocenic aminoalcohols has been performed. One step of this synthesis was a diastereospecific oxidation of diastereomeric mixtures of 1-[2-(N,N-dimethylaminomethyl)ferrocenyl]alcohols by manganese dioxide: one diastereomer was oxidized, while the other stayed inert. The six new chiral compounds in association with ZnEt2 proved to be good catalysts in the asymmetric ethylation of benzaldehyde (77 to 88% ee). (C) 1999 Elsevier Science Ltd.