Primary Aminomethylation at the α-Position of Carboxylic Acids and Esters. Trimethylsilyl Triflate-Catalyzed Reaction of Ketene Silyl Acetals with N, N-Bis (trimethylsilyl) methoxymethylamine

Abstract

A new, general method for the synthesis of β-aminocarboxylic esters (9) and acids (10) was developed. The introduction of a primary aminomethyl unit at the α-position of carboxylic esters (2) and acids (3) was achieved in high yields by the silyl trifluoromethanesulfonate (6)-catalyzed reaction of ketene silyl acetals (4) and ketene bissilyl acetals (5) with N, N-bis (trimethylsilyl)-methoxymethylamine (1). A possible mechanism for the reaction is proposed.