Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid

Saeedeh Torabi Kohlbouni; Aritra Sarkar; Jun Zhang; Xiaoyong Li; Babak Borhan

doi:10.1002/chir.23223

Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid

Chirality. 2020 Jun;32(6):817-823. doi: 10.1002/chir.23223. Epub 2020 Mar 22.

Authors

Saeedeh Torabi Kohlbouni¹, Aritra Sarkar¹, Jun Zhang¹, Xiaoyong Li², Babak Borhan¹

Affiliations

¹ Department of Chemistry, Michigan State University, East Lansing, Michigan, USA.
² Corteva Agriscience, Indianapolis, Indiana, USA.

PMID: 32201984
DOI: 10.1002/chir.23223

Abstract

Rapid derivatization of chiral 1,2-diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton-coupled circular dichroic (ECCD) of the naphthyl groups. Aryl- and alkyl-substituted 1,2-diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.

Keywords: ECCD; chiral sensing; chirality; dioxaborolane; stereochemistry.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

Grants and funding

CHE-1856335/National Science Foundation/International