2-amino-substituted 1-sulfinylferrocenes as chiral ligands in the addition of diethylzinc to aromatic aldehydes

J Org Chem. 2002 Feb 22;67(4):1346-53. doi: 10.1021/jo016271p.

Abstract

A simple and modulable access to a structural variety of enantiopure amino-substituted ferrocenyl sulfoxides and their use as chiral catalysts in the asymmetric addition of diethylzinc to aromatic aldehydes is described. Moderate to high enantioselectivities (up to 96% ee) were obtained in the case of the arylsulfonamide ligands (R(Fc), R(S))-4h and (R(Fc), R(S))-4i. It has been demonstrated that the planar chirality of the ferrocene unit is the decisive chiral element involved in the reaction.