title: A useful synthetic equivalent of a hydroxyacetone enolate.
abstract: Indium promoted allylation of carbonyl compounds with 4-(bromomethyl)-1,3-dioxol-2-one diastereoselectively affords anti-α,β-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldols.
authors.affiliation: Faculty of Chemistry, University of Belgrade, Studentski Trg 16, P. O. B. 51, 11158 Belgrade, Serbia.
authors.forename: Miljan
authors.initials: M
authors.lastname: Bigovic
authors.forename: Veselin
authors.initials: V
authors.lastname: Maslak
authors.forename: Zorana
authors.initials: Z
authors.lastname: Tokic-Vujosevic
authors.forename: Vladimir
authors.initials: V
authors.lastname: Divjakovic
authors.forename: Radomir N
authors.initials: RN
authors.lastname: Saicic
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000096:Acetone