title: Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.
abstract: Super silyl haloesters including chloro- and bromoacetate were synthesized and utilized for aldol reactions to give syn-β-hydroxy-α-haloacetates in good yields with high diastereoselectivities. β-Hydroxy-α-fluoroacetate was obtained by lithiation of super silyl bromofluoroacetate. Sequential Darzens reactions provided cis-glycidic esters in moderate yields.
authors.affiliation: Department of Chemistry, The University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States, and Molecular Catalyst Research Center, Chubu University , 1200 Matsumoto, Kasugai, Aichi 487-8501, Japan.
authors.forename: Susumu
authors.initials: S
authors.lastname: Oda
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry; D000447:Aldehydes; D004952:Esters; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000447:Aldehydes; D004952:Esters; D006842:Hydrocarbons, Brominated; D006843:Hydrocarbons, Chlorinated; D012821:Silanes; C016274:bromoacetate; C116609:3-hydroxybutanal