First Example of Stereoselective Aza-Perkow Reaction

摘要

Reactions of N-benzylpolychloroalkylimidoyl chlorides R_(Hlg)CCl=NCH_2Ph with trialkyl phosphites proceed unusually and, depending on the number of #alpha#-atoms of chlorine, yield either C,N-diphosphorylated vinylamides (R_(Hlg) = CCl_3) [1] or C-phosphorylated azadienes (R_(Hlg) = Me_2CCl) [2]. The behavior of N-benzyldichloroacetimidoyl chloride I in this reaction is of particular interest, because it furnishes information not only on the direction but also on stereochemistry of the process.