Efficient Transamination under Mild Conditions: Preparation of Primary Amine Derivatives from Carbonyl Compounds via Imine Isomerization with Catalytic Amounts of Potassium tert-Butoxide

Abstract

1,3-Prototropic rearrangement of N-diphenylmethanimines was successfully performed with a catalytic amount of potassium tert-butoxide. This procedure can also be used with aliphatic and aromatic aldimines and was extended to the isomerization of (1R)-camphorquinone monoimine and N-(4-methoxyphenyl)-4-phenyl-3-iminoazetidin-2-one. The isomerized imines were easily hydrolyzed and isolated as Cbz derivatives.