Wittig Reaction with N-Protected 3-(Triphenylphosphonio)alaninates : Synthesis of Optically Active (E)-(2-Arylvinyl)glycine Derivatives

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(R)-[2-Carboxy-2-[(methoxycarbonyl)amino]ethyl]triphenylphosphonium chloride (1) was converted by treatment with anion exchange resin (HCO^-_3) into the inner salt 13h, which gave a better yield (43%) than 1 in the Wittig reaction with benzaldehyde to afford the [S-(E)]-(2-phenylvinyl)glycine derivative 24. The inner salt 13i bearing an N-benzyloxycarbonyl group was prepared by hydrogenolysis of (R)-[3-benzyloxy-2-[(benzyloxycarbonyl)amino]-3-oxopropyl]triphenylphosphonium chloride (11e) over palladium on carbon, followed by dehydrochlorination. Hydrogenolysis of 11e over Pearlman's catalyst afforded the unprotected phosphonium chloride 12 (X=Cl). N-tert-Butoxycarbonylation of 12 followed by dehydrochlorination afforded 13j, which was more efficiently prepared through hydrogenolysis of (R)-[3-benzyloxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl]triphenylphosphonium chloride (11f).The usefulness of 13h-j as building blocks for the synthesis of configurationally labile (2-arylvinyl)glycine derivatives was exemplified by the Wittig reactions with piperonal, which exclusively afforded the (E)-isomers 18h-j with high optical purity in 28-39% yield.

収録刊行物

  • Chem. Pharm. Bull.

    Chem. Pharm. Bull. 41 252-261, 1993

    公益社団法人日本薬学会

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詳細情報 詳細情報について

  • CRID
    1570572702395738752
  • NII論文ID
    110003630384
  • NII書誌ID
    AA00602100
  • ISSN
    00092363
  • 本文言語コード
    en
  • データソース種別
    • CiNii Articles

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