Synthesis of N-substituted α,α-difluoro-β-aminophosphonates by addition of diethyl lithiodifluoromethylphosphonate to imines

Addition of diethyl lithiodifluoromethylphosphonate to N-substituted imines provides N-substituted α,α-difluoro-β-aminophosphonates. N-Alkyl, aryl, or Boc substituted aldimines give good to high yields in these reactions, while in ketimine series, only activated N-(2,2,2-trifluoro-1-phenylethylidene)aniline showed high reactivity.

Graphical abstractAddition of diethyl lithiodifluoromethylphosphonate to N-substituted aldimines or activated ketimines provides N-substituted α,α-difluoro-β-aminophosphonates.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Diethyl lithiodifluoromethylphosphonate adds to N-substituted imines to provide N-substituted α,α-difluoro-β-aminophosphonates. ► Reactions with N-aryl or N-alkyl aldimines provide high yields of products. ► In ketimine series only activated N-(2,2,2-trifluoro-1-phenylethylidene)aniline showed high reactivity.