title: Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives.
abstract: Both enantiomers of 3-hydroxyalkanoates and -alkanones were prepared by the diastereocontrolled addition of enolates to ketones containing (R)-6-methyl-1,3-oxathiane moiety as a chiral auxiliary; a formation of enolate from samarium(II) iodide and alpha-bromoamide is also discussed.
authors.affiliation: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto, Japan. matsubar@mc.kyoto-u.ac.jp
authors.forename: Seijiro
authors.initials: S
authors.lastname: Matsubara
authors.forename: Yuri
authors.initials: Y
authors.lastname: Kasuga
authors.forename: Takuya
authors.initials: T
authors.lastname: Yasui
authors.forename: Masahito
authors.initials: M
authors.lastname: Yoshioka
authors.forename: Bohari
authors.initials: B
authors.lastname: Yamin
authors.forename: Kiitiro
authors.initials: K
authors.lastname: Utimoto
authors.forename: Koichiro
authors.initials: K
authors.lastname: Oshima
mesh_terms: D000215:Acylation; D001685:Biological Factors / Q000138:chemical synthesis; D008958:Models, Molecular; D008968:Molecular Conformation; D010075:Oxathiins / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001685:Biological Factors; D010075:Oxathiins