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 journal › Article

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

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Circular Dichroism
Amines
Conformations
Nuclear magnetic resonance
Amino Acids

Keywords

  • Amino acid
  • Aziridine
  • Intramolecular interaction
  • Trifluoromethyl group

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of β-amino-α-trifluoromethyl-α-amino acids exhibiting intramolecular interaction of CF3 with NHβ. / Waki, Minoru; Katagiri, Toshimasa; Matsuno, Kenji; Miyachi, Hiroyuki.

In: Tetrahedron Letters, Vol. 55, No. 50, 10.12.2014, p. 6915-6918.

Research output: Contribution to journal › Article

Waki, M, Katagiri, T, Matsuno, K & Miyachi, H 2014, 'Synthesis of β-amino-α-trifluoromethyl-α-amino acids exhibiting intramolecular interaction of CF3 with NHβ', Tetrahedron Letters, vol. 55, no. 50, pp. 6915-6918. https://doi.org/10.1016/j.tetlet.2014.10.107
Waki M, Katagiri T, Matsuno K, Miyachi H. Synthesis of β-amino-α-trifluoromethyl-α-amino acids exhibiting intramolecular interaction of CF3 with NHβ. Tetrahedron Letters. 2014 Dec 10;55(50):6915-6918. https://doi.org/10.1016/j.tetlet.2014.10.107
Waki, Minoru ; Katagiri, Toshimasa ; Matsuno, Kenji ; Miyachi, Hiroyuki. / Synthesis of β-amino-α-trifluoromethyl-α-amino acids exhibiting intramolecular interaction of CF3 with NHβ. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 50. pp. 6915-6918.
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