1,4-Amino Alcohols with Cyclopropane Backbone for Diethylzinc Addition

Significance

A new type of ligand for asymmetric reactions was developed. 1,4-Amino alcohols with a cylopropane backbone were synthesized in three steps from readily available materials. This starting material is rather cheap because it is a synthetic intermediate of an insecticide. The synthetic scheme is amenable to variation of important features such as the amine substituents and the substituents on the alcohol carbon (in this case only H₂ and Ph₂ shown). The ligands proved to be good chiral inductors for the asymmetric addition of diethylzinc to aromatic aldehydes.