NDLI: Optimizing dirhodium(ii) tetrakiscarboxylates as chiral NMR auxiliaries

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Optimizing dirhodium(ii) tetrakiscarboxylates as chiral NMR auxiliaries

Content Provider	Royal Society of Chemistry (RSC)
Author	Fohrer, Joerg G. G. Gardiner, Michael G. Ghanem, Ashraf Duddeck, Helmut Mattiza, Jens T.
Copyright Year	2011
Abstract	Thirteen enantiopure paddlewheel-shaped dirhodium(II) tetrakiscarboxylate complexes have been checked for their efficiency in the dirhodium method (differentiation of enantiomers by NMR spectroscopy); six of them are new. Their diastereomeric dispersion effects were studied and compared via so-called key numbers KN. Adducts of each complex were tested with five different test ligands representing all relevant donor properties from strong (phosphane) to very weak (ether). Only one of them, the dirhodium complex with four axial (S)-N-2,3-naphthalenedicarboxyl-tert-leucinate groups (N23tL), showed results significantly better for all ligands than the conventional complex Rh* [Rh(II)2[(R)-(+)-MTPA]4; MTPA = methoxytrifluoromethylphenylacetate]. On the basis of 1H{1H} NOE spectroscopy and X-ray diffraction, a combination of favourable anisotropic group orientation and conformational flexibility is held responsible for the high efficiency of N23tL in enantiodifferentiation. Both complexes, Rh* and N23tL, are recommended as chiral auxiliaries for the dirhodium experiment.
Starting Page	6542
Ending Page	6550
Page Count	9
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	19
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c1ob05665d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	X-ray crystallography Spectroscopy Chiral auxiliary KN Ether Nuclear Overhauser effect NOE Phosphine Enantiomer Nuclear magnetic resonance spectroscopy Birefringence London dispersion force
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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