title: Highly diastereoselective epimerization: stereodivergent synthesis of alpha-hydroxy-beta-amino isopentanoic acid.
abstract: The high diastereoselectivity of the base-catalyzed epimerization of oxazolidin-2-ones 7 and 8 is shown to depend on the nature of the N-substituent (R group); when R = Bn, the 4,5-trans-product (4S,5R)-9 is formed, whereas when R = H the 4,5-cis-product (4S,5S)-10 is formed, both with >99:1 dr. The successful hydrolysis of the oxazolidin-2-one group in both cis- and trans-derivatives show this to be a stereodivergent route to enantiopure alpha-hydroxy-beta-amino isopentanoic acids (2R,3S)-1 and (2S,3S)-2.
authors.affiliation: Division of Applied Life Science (BK 21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University, 660-701, Korea.
authors.forename: Woo Duck
authors.initials: WD
authors.lastname: Seo
authors.forename: Marcus J
authors.initials: MJ
authors.lastname: Curtis-Long
authors.forename: Young Bae
authors.initials: YB
authors.lastname: Ryu
authors.forename: Jin Hwan
authors.initials: JH
authors.lastname: Lee
authors.forename: Min Suk
authors.initials: MS
authors.lastname: Yang
authors.forename: Woo Song
authors.initials: WS
authors.lastname: Lee
authors.forename: Ki Hun
authors.initials: KH
authors.lastname: Park
mesh_terms: D008968:Molecular Conformation; D023303:Oxazolidinones / Q000737:chemistry*; D010421:Pentanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D023303:Oxazolidinones; D010421:Pentanoic Acids; C520528:alpha-hydroxy-beta-amino isopentanoic acid