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.

Automated summary

A new method was developed for the stereoselective synthesis of isoxazolidine derivatives via Lewis acid-catalyzed 5-endo-dig reductive hydroalkoxylation cascade on propargylic N-hydroxylamine. This method provides an efficient approach to biologically active isoxazolidine scaffolds. The synthetic potential of this methodology was demonstrated by synthesizing 1,3-aminoalcohol, 4-aminotetrahydropyran, and sedamine natural products.