Journal
CHIRALITY
Volume 21, Issue 1, Pages 51-68Publisher
WILEY
DOI: 10.1002/chir.20605
Keywords
H-1 and C-13 NMR; enantiodifferentiation; chiral ethers; Pirkle's reagents; lanthanide shift reagents; dirhodium complexes; cyclodextrins; NMR in nonisotropic phases
Funding
- Deutsche Forscliungsgemeinschaft [98/30]
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Enantiomers of chiral ethers and acetals are notoriously difficult to differentiate because their reactivity is low and they are poor donors to any Lewis acid or metal ion. As an exception, epoxides are somewhat better donors. This review describes the properties of ethers, explains NMR methods for their chiral recognition and describes successful examples of ether differentiation. The majority of literature reports deals with chiral lanthanide shift reagents and dirliodium tetracarboxylate complexes, which were used as enantiopure auxiliaries to create diastereomeric adducts, with dispersed H-1 and C-13 NMR signals. The various methods are compared as to which is best suited for which purpose. Chirality 21:51-68, 2009. (C) 2008 Wiley-Liss, Inc.
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