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Direct enantioseparation of axially chiral 1,1'-biaryl-2,2'-diols using amidine-based resolving agents.

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.

SUBMITTER: Kodama K

PROVIDER: S-EPMC9033420 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Direct enantioseparation of axially chiral 1,1'-biaryl-2,2'-diols using amidine-based resolving agents.

Kodama Koichi K Takase Fusato F Hirose Takuji T

RSC advances 20210519 30

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 crystallo ...[more]

PMID: 35480945

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