Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives

Won Suk Kim, Jin Hee Lee, Jongmin Kang, Cheon Gyu Cho

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

3-Phenylamino-5-bromo-2-pyrone undergoes facile Diels-Alder cycloadditions with various electron deficient dienophiles to afford an array of functionally rich and stereochemically defined cycloadducts in good to excellent isolated yields. Due to the electron donacity of the amine group, it only proceeds in normal electron demand D-A cycloadditions. Subsequent ring openings with NaOMe provided constrained α-amino acid derivatives.

Original languageEnglish
Pages (from-to)1683-1687
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number8
DOIs
StatePublished - 16 Feb 2004

Keywords

  • 2-Pyrone
  • Constrained α-amino acid
  • Diels-Alder

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