Abstract
A convenient, high-yielding preparation of tert-butyl ((S)-1-((R)-oxiran-2-yl)-2-phenylethyl)carbamate is described. An efficient chiral inversion as the key step is furnished via Boc-involved neighboring group participation mediated by thionyl chloride. This preparation has significant advantages over the previously reported methods with respect to simplicity, cost efficiency, yield, and purification procedure as well as industry reliability.
GRAPHICAL ABSTRACT
ACKNOWLEDGMENTS
We thank Min Li, Yinli Lv, Weixia Liu, Wenlong Wang, and Xiangjun Wang for their support with NMR, HPLC, and LC-MS analysis. We also thank Jun He and Hai Sun for their help in the manuscript preparation.
SUPPORTING INFORMATION
Full experimental detail, 1H and 13C NMR spectra, HPLC conditions, and charts for this article can be accessed on the publisher’s website.