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Effective enantiodifferentiation of spirochalcogenuranes by the dirhodium method: Towards the determination of absolute configurations?
Author(s) -
Gáti Tamás,
Tóth Gábor,
Drabowicz Józef,
Moeller Stefan,
Hofer Edgar,
Polavarapu Prasad,
Duddeck Helmut
Publication year - 2005
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.20103
Subject(s) - chemistry , absolute configuration , chirality (physics) , adduct , enantiomer , dispersion (optics) , optical rotatory dispersion , spectroscopy , enantiomeric excess , absolute (philosophy) , computational chemistry , stereochemistry , enantioselective synthesis , organic chemistry , circular dichroism , catalysis , chiral symmetry , optics , philosophy , physics , epistemology , quantum mechanics , nambu–jona lasinio model , quark
The properties of chiral spirochalcogenuranes acting as ligands in adducts with a chiral dirhodium tetracarboxylate complex is explored, and the individual adduct species are characterized by low‐temperature NMR spectroscopy. Chiral recognition and the determination of enantiomeric composition of the chiral spirochalcogenuranes is easy by evaluating NMR signal dispersions both at low and at room‐ or slightly elevated temperatures. The uniformity in the signs of 1 H dispersion effects and taking reference to the spiroselenurane with known absolute configuration [(S)‐(–)‐ 2 ] indicates that a convenient rule for the determination of absolute configuration in the spirochalcogenurane system can be established on the basis of 1 H chemical shift dispersions. Chirality 17:S40–S47, 2005. © 2005 Wiley‐Liss, Inc.