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- W1967038562 abstract "Axially chiral 2′-methoxy-1,1′-binaphthyl-2-carboxylic acid (1) was effectively utilized as chiral derivatizing agent for discrimination of enantiomeric alcohols and amines by 1H NMR with the aid of Eu(fod)3. Among a pair of the diastereomeric esters or amides prepared from (aS)-1 and an α-chiral alcohol or amine, the methoxyl protons of the (aS,R)-diastereomer showed the larger lanthanoid-induced downfield shift than those of the (aS,S)-counterpart. Thus, addition of up to 0.5–1.0 equiv amount of Eu(fod)3 caused base-line separation of those protons, allowing determination of the enantiomeric purities and assignment of the absolute configurations of the enantiomeric alcohols and amines. An X-ray crystallographic analysis of the amide ((aS,S)-2) obtained from (aS)-1 and (S)-1-phenylethylamine showed structural resemblance between the amides and esters of 1. Steric models which explain the NMR behavior of the diastereomeric esters and amides are presented based on X-ray analyses. Also reported are two methods to regenerate free acid 1 from amide 2 to afford axially homochiral 1." @default.
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- W1967038562 date "1989-12-01" @default.
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- W1967038562 title "Use of Axially Chiral 2′-Methoxy-1,1′-binaphthyl-2-carboxylic Acid as Chiral Derivatizing Agent for Discrimination of Enantiomeric Alcohols and Amines by<sup>1</sup>H NMR" @default.
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- W1967038562 doi "https://doi.org/10.1246/bcsj.62.3886" @default.
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