Chiral Silylation Reagents for the Determination of Absolute Configuration by NMR Spectroscopy

We have investigated the use of chiral silylating reagents as analytical probes for determining the absolute stereochemistry of natural products by NMR spectroscopy. These reagents are prepared in high chemical yield in one step and can be used to derivatize chiral allylic alcohols which are incompatible with ester-based methodologies. Microscale ( approximately 400 nmol) derivatization conditions have been defined. The resulting siloxane diastereomers are readily distinguished by their (1)H NMR spectra.