Stereoselective Horner-Wadsworth-Emmons Reaction of Dianions of Phosphonoacetic Acids

DOI
  • Sano Shigeki
    Faculty of Pharmaceutical Sciences, The University of Tokushima
  • Takemoto Yuka
    Faculty of Pharmaceutical Sciences, The University of Tokushima
  • Kujime Eiko
    Faculty of Pharmaceutical Sciences, The University of Tokushima
  • Nakano Fumihito
    Faculty of Pharmaceutical Sciences, The University of Tokushima
  • Nagao Yoshimitsu
    Faculty of Pharmaceutical Sciences, The University of Tokushima

Bibliographic Information

Other Title
  • ホスホノ酢酸ジアニオンを用いる立体選択的ＨＷＥ反応

Description

We have developed the stereoselective Horner–Wadsworth–Emmons (HWE) reaction of aldehydes with 2-fluoro-2-diethylphosphonoacetic acid (1) employing i-PrMgBr for the synthesis of (Z)-α-fluoro-α,β-unsaturated carboxylic acids as the major products. (E)-α,β-unsaturated carboxylic acids were obtained by the HWE reactions of aryl alkyl ketones with bis(2,2,2-trifluoroethyl)phosphonoacetic acid (2) utilizing lithium hexamethyldisilazide in N,N-dimethylformamide. Phosphonoacetic acid 2 was prepared by enzymatic hydrolysis of the corresponding methyl ester with porcine liver esterase (PLE). In addition, a novel P-chiral HWE reagent was synthesized by the PLE-promoted kinetic resolution of racemic phosphonates.

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Keywords

Details 詳細情報について

  • CRID
    1390282680610048000
  • NII Article ID
    130006995369
  • DOI
    10.14895/hannou.29.0.154.0
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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