Chiral silylation reagents: determining configuration via NMR-spectroscopic coanalysis

Organic Letters
F C SchroederJ Meinwald

Abstract

[structure: see text]Derivatization with (+)- and (-)-chloromenthoxydiphenylsilane was used to determine the absolute configuration of the insect defensive agent pinoresinol (1). Although the (1)H NMR chemical shift differences of the resulting two diastereomers are small, (1)H NMR spectroscopy provided for the unambiguous assignment of the natural product's configuration. For this purpose, a new approach involving NMR spectra of mixtures of diastereomers was used. Our method resembles coinjecting mixtures of samples of known and unknown configuration in GC and HPLC.

Citations

Nov 6, 2007·Proceedings of the National Academy of Sciences of the United States of America·Christopher D CainNeal S Bricker
Oct 13, 2006·Proceedings of the National Academy of Sciences of the United States of America·Frank C SchroederThomas Eisner
Oct 18, 2007·Proceedings of the National Academy of Sciences of the United States of America·Cécile BertinFrank C Schroeder
Jan 13, 2006·Nature Chemical Biology·Peter W SorensenThomas R Hoye
Sep 21, 2010·Chirality·Thomas J Wenzel, Cora D Chisholm
Aug 24, 2007·Organic Letters·Maurizio CampagnaStefan Bienz
Jul 30, 2010·ACS Chemical Biology·Christen Brownlee

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