A One-Pot, Three-Step Synthesis of α-Aminophosphonic Acids

Abstract

A total of 20 α-aminophosphonic acids are synthesized in 73–89% yields via a one-pot, three-step procedure involving chlorotrimethylsilane-promoted condensation of carbonyl compounds and primary amines yielding azomethine intermediates, subsequent reaction with tris(trimethylsilyl) phosphite to give the corresponding trimethylsilylphosphonic esters and finally, mild cleavage with methanol–water. The wide scope and simple set-up and work-up procedures of the reported method allow the synthesis of a diverse set of α-aminophosphonic acids possessing two different functional groups.

Key words

α-aminophosphonic acids - aldehydes - amines - chlorotrimethylsilane - tris(trimethylsilyl) phosphite - one-pot synthesis

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