Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization

Osamu Kitagawa, Tokushi Hanano, Norihiko Kikuchi, Takeo Taguchi

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The α-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I2 and s-collidine. The chiral iodides 2 thus obtained were converted to the α-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.

Original languageEnglish
Pages (from-to)2165-2168
Number of pages4
JournalTetrahedron Letters
Issue number13
Publication statusPublished - 1993 Mar 26



  • asymmetric iodination
  • chiral pyrrolidine
  • iodolactonization
  • α-amino acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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