Chiral recognition of olefins by 1H NMR spectroscopy in the presence of a chiral dirhodium complex

A new NMR method using 1 for chiral recognition of olefins is presented and compared with Mannschreck's method using Yb(hfc) 3/Ag(fod). It was found that the spectroscopic results are comparable but the new rhodium reagent is much easier to handle and can readily be recovered. New method for th...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 5; no. 1; pp. 27 - 30
Main Authors Wypchlo, Klaudia, Duddeck, Helmut
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 1994
Elsevier Science
Subjects
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
1,8-p-Menthadiene
Hydrocarbon
Organic ligand
Transition metal Complexes
Dienic compound
p-Mentha-6,8-dien-2-one
Mu complex
Rhodium Complexes
Chirality
Enantiomer
Metal metal bond
Carboxylate
Bicyclic compound
Monoterpene
Platinoid Complexes
NMR spectrum
Enone
Monocyclic compound
Ethylenic compound
Recognition
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Summary:A new NMR method using 1 for chiral recognition of olefins is presented and compared with Mannschreck's method using Yb(hfc) 3/Ag(fod). It was found that the spectroscopic results are comparable but the new rhodium reagent is much easier to handle and can readily be recovered. New method for the determination of the enantiomeric purity of olefins Examples: α-pinene, limonene, 4-vinyl-1-cyclohexene and carvone; camphene fails
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(00)80477-2