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Geometric enantiomerism in cyclic compounds: Chiral dibrominated 1,3‐dioxanes
Author(s) -
Cismaş Crina,
Vanthuyne Nicolas,
Rispaud Hélène,
Varga Richard Attila,
Bogdan Elena,
Roussel Christian,
Grosu Ion
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20895
Subject(s) - chemistry , diastereomer , enantiomer , chirality (physics) , halogenation , stereochemistry , chiral column chromatography , solid state , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
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. Chirality, 2011. © 2010 Wiley‐Liss, Inc.