The dirhodium-method in the determination of absolute configurations of phospholene chalcogenides

Chirality
Stefan MoellerHelmut Duddeck

Abstract

The 1H, 13C, and 31P NMR signals of six chiral phospholene chalcogenides (X = O, S, Se) are duplicated in the presence of one mole equivalent of the chiral auxiliary Rh2[(R)-MTPA]4 (diastereomeric dispersion Deltanu; in Hz). The samples were investigated as nonracemic mixtures of enantiomers with known absolute configurations so that signs can be attributed to the Deltanu-values and each signal set can be assigned to the respective enantiomer. The signs are uniform--in particular those of 1H nuclei--and nearly independent of the nature of the chalcogen atom. Thus, if the absolute configuration of one compound is known, it is possible to derive absolute configurations in the whole series (correlation method).

References

Jun 8, 2004·Magnetic Resonance in Chemistry : MRC·Tamás GátiHelmut Duddeck
Nov 10, 2005·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Helmut Duddeck

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Citations

Aug 3, 2011·Organic & Biomolecular Chemistry·Jens T MattizaAshraf Ghanem
Dec 17, 2008·Magnetic Resonance in Chemistry : MRC·Edison Díaz Gómez, Helmut Duddeck
Aug 15, 2013·Magnetic Resonance in Chemistry : MRC·Jarosław Jaźwiński, Agnieszka Sadlej
Sep 21, 2010·Chirality·Thomas J Wenzel, Cora D Chisholm
Apr 14, 2010·Chemical Reviews·L Kollár, G Keglevich
Jun 8, 2017·Journal of the American Chemical Society·Kelvin Meng-Hui Lim, Tamio Hayashi

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