Geometric enantiomerism in cyclic compounds: chiral dibrominated 1,3-dioxanes.
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.
Cismaş
Crina
C
Faculty of Chemistry and Chemical Engineering, Center of Supramolecular Organic and Organometallic Chemistry, Babes-Bolyai University, Cluj-Napoca, Romania.
Vanthuyne
Nicolas
N
Rispaud
Hélène
H
Varga
Richard Attila
RA
Bogdan
Elena
E
Roussel
Christian
C
Grosu
Ion
I
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
D004146:Dioxanes; D006573:Heterocyclic Compounds, 1-Ring; D001966:Bromine