Synthesis of Enantiopure 1-Aryl-l-butylamines and l-Aryl-3-butenylamines by Diastereoselective Addition of Allylzinc Bromide to Imines Derived from (R)-Phenylglycine Amide

摘要

The synthesis of enantiopure 1-aryl-l-butylamines via a highly diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide is reported. These are synthesised by a three-step procedure, which involves: (a) formation of the chiral imines; (b) asymmetric addition of the allylzinc reagent; (c) removal of the chiral auxiliary by means of a reductive or non-reductive method. The reductive method provides 1-aryl-l-butylamines whereas the non-reductive method preserves the double bond to afford 1-aryl-3-butenylamines.