Access to Fluoropyrrolidines by Intramolecular Aza-Michael Addition Reaction

Study of the intramolecular aza-Michael addition reaction from an aminofluorovinylsulfone opens a new route for the synthesis of pyrrolidine derivatives. An unexpected diastereoselective cyclization reaction was observed, leading preferentially to the anti-N-benzylpyrrolidine sulfone. The resulting sulfone was reacted with aldehydes to access beta-substituted alpha-fluoroalkenyl pyrrolidines in one step.