Direct enantioseparation of axially chiral 1,1′-biaryl-2,2′-diols using amidine-based resolving agents |
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Authors: | Koichi Kodama Fusato Takase Takuji Hirose |
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Institution: | Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Japan, |
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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.Enantioseparation of atropisomeric biphenols using a chiral amidine derived from dehydroabietic acid was reported. Only one crystallization of their mixture gave pure diastereomeric salts of biphenols from racemate. |
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