An Efficient Synthesis ofN-Phosphorylated Azadienes, Primary (E)-Allylamines, and β-Amino-Phosphane Oxides and -Phosphonates from β-Functionalized Oxime Derivatives

A simple and stereoselective synthesis of primary (E)-allylamines 1 and 1-azadienes 5, 7 is reported. N-Phosphorylated azadienes 5 and 7 are obtained by addition of phosphorus chlorides 3 to unsaturated oximes 2, while azadienes 24 are prepared by olefination reactions of functionalized enamines 20/21. Reduction of azadienes 5, 7, 24 and derivatives 13/14 and 20/21 with hydrides, followed by deprotection of the resulting amines leads to the formation of primary allylamines 1 and β-aminophosphane oxides 17, phosphonates 18, and phosphonic acid derivatives 19.