title: Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction.
abstract: A palladium-catalyzed hydroamination reaction is the key step in a stereoselective synthesis of 2,5-disubstituted and 2,3,5-trisubsituted morpholines from carbamate-protected aziridines. Aziridines are selectively attacked at the more substituted position by unsaturated alcohol nucleophiles using Lewis acid catalysts. Palladium-catalyzed hydroamination of the resulting aminoalkenes gives morpholines as a single diastereomer in excellent yield.
authors.affiliation: Department of Chemistry, University of Washington, Box 351700, Seattle, WA 98195-1700, USA.
authors.forename: Alicia
authors.initials: A
authors.lastname: McGhee
authors.forename: Brian M
authors.initials: BM
authors.lastname: Cochran
authors.forename: Torrey A
authors.initials: TA
authors.lastname: Stenmark
authors.forename: Forrest E
authors.initials: FE
authors.lastname: Michael
mesh_terms: D000586:Amination; D002384:Catalysis; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009025:Morpholines; D010165:Palladium; C037574:morpholine