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Paper | Regular issue | Vol 98, No. 9, 2019, pp.1215-1227
Published online, 26th September, 2019
DOI: 10.3987/COM-19-14148
Direct Determination of the Absolute Configurations of Chiral Cyanohydrins Using Bis(zinc porphyrin) as a CD-Sensitive Bidentate Host

Satoshi Hayashi, Shiori Takeda, Masahiro Noji,* and Toshikatsu Takanami*

*Department of Life and Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

The absolute configurations of cyanohydrins are readily determined via an exciton-coupled circular dichroism (ECCD) protocol using bidentate bis(zinc porphyrin) host molecule BP1 as a CD-sensitive chirality probe. UV–vis and NMR studies revealed a monodentate binding mode of cyanohydrin with BP1. Based on these studies, a simple working model using a Newman projection of cyanohydrins was established, allowing BP1 to determine the stereochemistry of various cyanohydrins in a non-empirical and unambiguous manner.