Synthesis of trisubstituted allenamides utilizing 1,2-rearrangement of dialkoxyphosphoryl moiety under Brønsted base catalysis

A new method for the synthesis of trisubstituted allenamides was developed by utilizing the 1,2-rearrangement of a dialkoxyphosphoryl moiety from carbon to nitrogen under Brønsted base catalysis. The reaction would involve the catalytic generation of an α-amino propargyl anion through the key rearrangement, the addition to an electrophile at the α-position of the anionic intermediate, and the unprecedented rearrangement of a phosphoramidate moiety of the adduct, providing trisubstituted allenamides that are difficult to synthesize by using conventional methods.