title: Catalytic enantioselective [2,3]-rearrangements of amine N-oxides.
abstract: The first Pd-catalyzed enantioselective [2,3]-rearrangement of allylic amine N-oxides is described, which formally represents an asymmetric Meisenheimer rearrangement. The mild reaction conditions enable the synthesis of chiral nonracemic aliphatic allylic alcohol derivatives with reactive functional groups. On the basis of preliminary studies, a cyclization-mediated mechanism is proposed.
authors.affiliation: Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.
authors.forename: Hongli
authors.initials: H
authors.lastname: Bao
authors.forename: Xiangbing
authors.initials: X
authors.lastname: Qi
authors.forename: Uttam K
authors.initials: UK
authors.lastname: Tambar
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D009584:Nitrogen / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000588:Amines; D010087:Oxides; D009584:Nitrogen