Synthesis, Structure and Application of α, β Dehydro-α-aminophosphonic and α,β-Dehydro-α-aminophosphinic Acid Derivatives

Abstract

The synthesis of α,β-dehydro-α-aminophosphonic and α,β-dehydro-α-aminophosphinic acid derivatives is discussed. The most important synthetic pathways to the above-mentioned compounds have been divided into four groups depending on the type of bond formed as the last one. The configuration at the C=C double bond can be established based on the specific coupling constants 3JHP and 3JCP for the appropriate Z- and E-stereoisomers. The application of α,β-dehydro-α-aminophosphonates and α,β-dehydro-α- aminophosphinates, particularly in the enantioselective catalytic hydrogenation, is also discussed. Keywords: α -aminophosphinic acids, α -aminophosphonic acids, asymmetric catalytic hydrogenation, α , β -dehydro-α-aminophosphinates, α, β-dehydro-α-aminophosphonates, Michaelis-Arbuzov reaction, Wadsworth-Emmons reaction.