Coumarin-Containing Chiral Discriminating Agents. VII. New Crystalline <SUP>1</SUP>H-NMR Enantiomeric Excess Determination Reagent for Alcohols and Amines, (R)-(-)- and (S)-(+)-O-Coumarinylmandelic Acids

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  • クマリン骨格を有する光学異性体識別試薬の開発研究.第7報.<SUP>1</SUP>H-NMRを利用したアルコール・アミン類に対する新規, 結晶性キラル誘導化試薬, (R)-(-)及び(S)-(+)-O-クマリルマンデル酸
  • クマリン骨格を有する光学異性体識別試薬の開発研究-第7報-1H-NMRを利用したアルコール・アミン類に対する新規,結晶性キラル誘導化試薬,(R)-(-)及び(S)-(+)-O-クマリルマンデル酸
  • クマリン コッカク オ ユウスル コウガク イセイタイ シキベツ シヤク ノ

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Description

The Mitsunobu reaction of commercial 4-hydroxycoumarin with both (R)-(-)- and (S)-(+)-tert-butyl mandelates derived from commercial enantiopure mandelic acids furnished (S)-(+)- and (R)-(-)-tert-butyl O-coumarinylman-delates which were, then, treated with trifluoroacetic acid to give novel crystal-line optically pure (S)-(+)- and (R)-(-)-O-coumarinylmandelic acids [SCMOH and RCMOH], respectively in good overall yields. Diastereotopic nonequivalence 1H-NMR examination of the resultant esters and amides without any racemization or kinetic resolution by way of a Steglich's procedure (a DCC-DMAP method) has proved each acid to be a useful, efficient and reliable chiral derivatizing agent for the enantiomeric excess determination of chiral alcohols and amines.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 117 (10-11), 786-799, 1997

    The Pharmaceutical Society of Japan

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