title: Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction.
abstract: A reagent-controlled, diastereo- and enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates has been achieved by the proper choice of solvent, temperature, alkoxy group, and amine for the diisopinocampheylboron-mediated asymmetric enolization-aldolization of phenylacetates. The pure diastereomers can be readily separated by column chromatography.
authors.affiliation: Hebert C. Brown Centre for Borane Research, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA. chandran@purdue.edu
authors.forename: P Veeraraghavan
authors.initials: PV
authors.lastname: Ramachandran
authors.forename: Prem B
authors.initials: PB
authors.lastname: Chanda
mesh_terms: D000438:Alcohols / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D001896:Boron Compounds; D002264:Carboxylic Acids; D007659:Ketones