title: Ruthenium-catalyzed asymmetric N-demethylative rearrangement of isoxazolidines and its application in the asymmetric total syntheses of (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12.
abstract: An asymmetric N-demethylative rearrangement of 1,2-isoxazolidines catalyzed by ruthenium is described. Enantioenriched syn-1,3-aminoalcohols as well as cis-1,3-oxazinanes, which are useful building blocks, can be efficiently prepared stereospecifically by this reaction in good yields, via the isoxazolidine intermediates in situ generated from a nitrone bearing a chiral auxiliary and styrenes. This asymmetric reaction was also applied in the asymmetric total syntheses of both (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12.
authors.affiliation: Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
authors.forename: Zu-Feng
authors.initials: ZF
authors.lastname: Xiao
authors.forename: Chuan-Zhi
authors.initials: CZ
authors.lastname: Yao
authors.forename: Yan-Biao
authors.initials: YB
authors.lastname: Kang
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D007555:Isoxazoles; D010078:Oxazines; D012428:Ruthenium