title: Geometric enantiomerism in cyclic compounds: chiral dibrominated 1,3-dioxanes.
abstract: The first geometric enantiomers in the cyclic compounds series are reported. The investigated compounds are 2,2-disubstituted-5-methyl-1,3-dioxane derivatives in which the substituents at position 2 bear chiral centers with identical substituents but with opposite configurations. The structure of the unlike isomers was determined from the solid state molecular structure of the compounds obtained by single crystal X-ray diffractometry and the enantiomers of these diastereoisomers were observed by chiral column HPLC base-line separation. The investigated compounds were obtained by a diastereoselective bromination reaction of the corresponding 2,2-dialkyl and 2,2-dibenzyl-5-methyl-1,3-dioxanes.
authors.affiliation: Faculty of Chemistry and Chemical Engineering, Center of Supramolecular Organic and Organometallic Chemistry, Babes-Bolyai University, Cluj-Napoca, Romania.
authors.forename: Crina
authors.initials: C
authors.lastname: Cismaş
authors.forename: Nicolas
authors.initials: N
authors.lastname: Vanthuyne
authors.forename: Hélène
authors.initials: H
authors.lastname: Rispaud
authors.forename: Richard Attila
authors.initials: RA
authors.lastname: Varga
authors.forename: Elena
authors.initials: E
authors.lastname: Bogdan
authors.forename: Christian
authors.initials: C
authors.lastname: Roussel
authors.forename: Ion
authors.initials: I
authors.lastname: Grosu
mesh_terms: D001966:Bromine / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004146:Dioxanes / Q000737:chemistry*; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D004146:Dioxanes; D006573:Heterocyclic Compounds, 1-Ring; D001966:Bromine