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Updated: Sep 25, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Direct enantioseparation of axially chiral 1,1'-biaryl-2,2'-diols using amidine-based resolving agents
Koichi Kodama1, Fusato Takase1, Takuji Hirose1
1Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University Japan kodama@mail.saitama-u.ac.jp.
Abstract:
Amidine-based optically active resolving agents for enantiomer separation of axially chiral 1,1'-biaryl-2,2'-diols have been developed. A strongly basic amidine bearing no substituents on its nitrogen atoms enables the formation of their diastereomeric salts upon being mixed with weakly acidic phenol derivatives. Enantiopure 1,1'-biaryl-2,2'-diols can be obtained in high yields after only one crystallization of their salts with the chiral amidine derived from dehydroabietic acid. X-ray crystallography revealed that the amidine moiety forms a salt with the phenol group and additional intermolecular NH/π interactions contribute to the efficient chiral recognition process.
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