title: Stereoselective isoxazolidine synthesis via copper-catalyzed alkene aminooxygenation.
abstract: Isoxazolidines are useful in organic synthesis, drug discovery, and chemical biology endeavors. A new stereoselective synthesis of methyleneoxy-substituted isoxazolidines is disclosed. The method involves copper-catalyzed aminooxygenation/cyclization of N-sulfonyl-O-butenyl hydroxylamines in the presence of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl radical (TEMPO) and O(2) and provides substituted isoxazolidines in excellent yields and diastereoselectivities. We also demonstrate selective mono N-O reduction followed by oxidation of the remaining N-O bond to reveal a 2-amino-γ-lactone. Reduction of the γ-lactone reveals the corresponding aminodiol.
authors.affiliation: Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, USA.
authors.forename: Shuklendu D
authors.initials: SD
authors.lastname: Karyakarte
authors.forename: Thomas P
authors.initials: TP
authors.lastname: Smith
authors.forename: Sherry R
authors.initials: SR
authors.lastname: Chemler
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000588:Amines; D010080:Oxazoles; D003300:Copper; D010100:Oxygen