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.
Baker Laboratory, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.
D B
DB
Weibel
T R
TR
Walker
F C
FC
Schroeder
J
J
Meinwald
D000818:Animals; D001685:Biological Factors / Q000737:chemistry / Q000378:metabolism; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D018942:Macrolides / Q000737:chemistry* / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D020005:Propanols / Q000737:chemistry / Q000378:metabolism; D012833:Siloxanes / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
D001685:Biological Factors; D004952:Esters; D018942:Macrolides; D020005:Propanols; D012833:Siloxanes; C006463:allyl alcohol