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Chiral recognition of ethers by NMR spectroscopy
Author(s) -
Duddeck Helmut,
Díaz Gómez Edison
Publication year - 2009
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.20605
Subject(s) - chemistry , enantiopure drug , diastereomer , adduct , lanthanide , lewis acids and bases , nuclear magnetic resonance spectroscopy , reactivity (psychology) , enantiomer , reagent , ether , chiral derivatizing agent , organic chemistry , chiral auxiliary , chiral column chromatography , catalysis , ion , enantioselective synthesis , medicine , alternative medicine , pathology
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 dirhodium tetracarboxylate complexes, which were used as enantiopure auxiliaries to create diastereomeric adducts with dispersed 1 H and 13 C NMR signals. The various methods are compared as to which is best suited for which purpose. Chirality, 2009. © 2008 Wiley‐Liss, Inc.