Asymmetric Cyclization <i>via</i> Preservation of Chirality

DOI

Bibliographic Information

Other Title
  • 分子内アルキル化における不斉の保持
  • A Concise Access to Chiral Nitrogen-Containing Heterocycles
  • キラル含窒素複素環の簡便合成

Abstract

A new method for asymmetric cyclization was developed based on dynamic chirality of enolates derived from α-amino acids. N-(ω-bromoalkyl)-amino acid derivatives, readily prepared from natural α-amino acids, gave cyclic amino acids with a quaternary stereo-center by the treatment with potassium hexamethyldisilazaide (KHMDS). Chirality of parent amino acids was almost completely preserved during enolate-formation and cyclization process, giving cyclic amino acids in up to 98% ee in retention of configuration. This method is applicable to the asymmetric synthesis of azetidine, pyrrolidine, piperidine, and azepane derivatives. Similarly, a route to highly substituted chiral nitrogen-containing heterocycles was developed through intramolecular conjugate addition of chiral enolates derived from α-amino acids.

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Keywords

Details 詳細情報について

  • CRID
    1390282680611470848
  • NII Article ID
    130006997192
  • DOI
    10.14895/hannou.29.0.208.0
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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