Lewis-Acid-Catalyzed Reductive Hydroalkoxylation of Propargylic N -Hydroxylamines Gives Stereoselective Access to Isoxazolidines.

Lewis-acid-catalyzed 5 -endo-dig reductive hydroalkoxylation cascade on propargylic N -hydroxylamine gave expedient, stereoselective access to isoxazolidine derivatives. The developed method provides a new approach toward the synthesis of isoxazolidine, a biologically privileged scaffold. The synthetic potential of the developed methodology was demonstrated by synthesizing 1,3-aminoalcohol, 4-aminotetrahydropyran, and sedamine natural products.