Lewis-Acid-Catalyzed Reductive Hydroalkoxylation of Propargylic <i>N</i>-Hydroxylamines Gives Stereoselective Access to Isoxazolidines
Santosh J. Gharpure, Dharmendra S. Vishwakarma, Showkat A. Hajam
Abstract
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.
Topics & Concepts
ChemistryStereoselectivityHydroxylamineCatalysisLewis acids and basesCombinatorial chemistryOrganic chemistryStereochemistrySynthetic Organic Chemistry MethodsMicrobial Natural Products and BiosynthesisOxidative Organic Chemistry Reactions