Thionyl Chloride–Mediated Synthesis of tert-Butyl ((S)-1-((R)-Oxiran-2-yl)-2-phenylethyl)carbamate with Boc-Involved Neighboring Group Participation

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

Keywords:

• Chiral inversion
• chiral retention
• neighboring group participation
• thionyl chloride

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.