Use of axially chiral 2'-methoxy-1,1'-binaphthyl-2-carboxylic acid as chiral derivatizing agent for discrimination of enantiomeric alcohols and amines by 1H NMR.

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概要

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• Axially chiral 2′-methoxy-1,1′-binaphthyl-2-carboxylic acid (<B>1</B>) was effectively utilized as chiral derivatizing agent for discrimination of enantiomeric alcohols and amines by <SUP>1</SUP>H NMR with the aid of Eu(fod)<SUB>3</SUB>. Among a pair of the diastereomeric esters or amides prepared from (a<I>S</I>)-<B>1</B> and an α-chiral alcohol or amine, the methoxyl protons of the (a<I>S</I>,<I>R</I>)-diastereomer showed the larger lanthanoid-induced downfield shift than those of the (a<I>S</I>,<I>S</I>)-counterpart. Thus, addition of up to 0.5–1.0 equiv amount of Eu(fod)<SUB>3</SUB> 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 ((a<I>S</I>,<I>S</I>)-<B>2</B>) obtained from (a<I>S</I>)-<B>1</B> and (<I>S</I>)-1-phenylethylamine showed structural resemblance between the amides and esters of <B>1</B>. 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 <B>1</B> from amide <B>2</B> to afford axially homochiral <B>1</B>.

• 公益社団法人 日本化学会の論文

著者

• KABUTO Chizuko

  Department of Chemistry, Faculty of Science, Tohoku University

• Miyano Sotaro

  Department Of Biochemistry And Engineering Faculty Of Engineering Tohoku University

• Okada Shin-ichi

  Department Of Neuro-psychiatry School Of Medicine Chiba University

• Kabuto Chizuko

  Department Of Chemistry Faculty Of Science Tohoku University

• Hotta Hiroki

  Department Of Biochemistry Kyoto Prefectural University

• Yasuhara Fujiko

  Department Of Chemistry College Of General Education Tohoku University

• Takeda Masayuki

  Department Of Biochemistry And Engineering Faculty Of Engineering Tohoku University

• Suzuki Takatsugu

  Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University

• Hotta Hiroki

  Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University

• Miyano Sotaro

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

• Okada Shin-ichi

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

• Okada Shin-ichi

  Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University

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