(2R,3S)-3,4,4,4-Tetrafluorovaline: A Fluorinated Bioisostere of Isoleucine

Lennart Brewitz, Hidetoshi Noda, Naoya Kumagai, Masakatsu Shibasaki

研究成果: Article査読

抄録

The synthesis of (2R,3S)-3,4,4,4-tetrafluorovaline, a fluorinated derivative of the canonical α-amino acid l-valine, is reported for the first time. A highly enantio- and diastereoselective direct catalytic asymmetric Mannich-type reaction was applied as the key C–C bond-forming step to afford gram quantities of a central synthetic intermediate. The conformation of the novel fluorinated α-amino acid was analyzed by X-ray crystallography, NMR spectroscopy, and computational methods, which, together with its calculated and experimental physicochemical properties, indicated that the fluorinated valine is a bioisostere of l-isoleucine.

本文言語English
ページ(範囲)1745-1752
ページ数8
ジャーナルEuropean Journal of Organic Chemistry
2020
11
DOI
出版ステータスPublished - 2020 3 22
外部発表はい

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 有機化学

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