Synthesis of β-amino-α-trifluoromethyl-α-amino acids exhibiting intramolecular interaction of CF3 with NHβ

Minoru Waki, Toshimasa Katagiri, Kenji Matsuno, Hiroyuki Miyachi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

We prepared β-amino-α-trifluoromethyl-α-amino acids through ring-opening reaction of N-tosyl-2-trifluoromethyl-2-ethoxycarbonylaziridine with aromatic and benzylic amines, and investigated the intramolecular interaction between the trifluoromethyl (CF3) group at the α-position and the NH group at the β-position (NHβ). NMR, UV/vis, and circular dichroism measurements indicated that the conformation of these compounds is fixed by intramolecular interaction of CF3 with NHβ to form a six-membered ring.

Original languageEnglish
Pages (from-to)6915-6918
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number50
DOIs
Publication statusPublished - Dec 10 2014

Keywords

  • Amino acid
  • Aziridine
  • Intramolecular interaction
  • Trifluoromethyl group

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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