ORGN 79 |
| A practically simple three-component chiral derivatizing protocol for determining the enantiopurity of chiral primary amines, chiral 1,2-, 1,3- and 1,4-diols by 1H NMR spectroscopic analysis is described. Chiral primary amines, chiral 1,2-, 1,3- and 1,4-diols have many important chemical and pharmaceutical applications, and as a consequence, a wide range of methodologies have been developed for their asymmetric synthesis. Therefore, the development of inexpensive chiral derivatisation protocols that enable their enantiomeric excess (ee) to be simply determined by NMR spectroscopic analysis is currently of great interest to the synthetic community. The most widely used chiral derivatizing agent (CDA) for determining the enantiomeric purity of chiral amines and diols using NMR spectroscopy involves derivatisation to afford either MTPA (Mosher) or MPA (Trost) amides or esters respectively. Despite its popularity, this methodology has its limitations, including the expense and moisture sensitivity of the acid chloride reagents, the potential for kinetic resolution and the need to run both 1H and 19F NMR experiments for an accurate determination of enantiomeric purity.
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Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Sunday, 10 September 2006 Moscone Center -- Room 131, Oral
Division of Organic Chemistry |
