1,3-asymmetric induction—VI : Stereochemistry of the reactions between organo-metals and β-asymmetric amino-ketones

The stereochemical course of the reaction between organo-metals and β-asymmetric amino-ketones has been investigated by varying the nature of the reagent and the substituents in the substrate, as well as the distance of the amino-group from the reaction center.The relative configurations of the diastereomeric amino-alcohols obtained were assigned, thus determining the direction of the predominant attack by the nucleophile.The stereoselectivity was found to be strongly dependent on the factors investigated, particularly on the nature of the amino-group and of the reagent.No single model of asymmetric induction proved to be suitable for the prediction of the stereochemical results in the above reactions.