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

Minoru Waki; Toshimasa Katagiri; Kenji Matsuno; Hiroyuki Miyachi

doi:10.1016/j.tetlet.2014.10.107

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

Minoru Waki, Toshimasa Katagiri, Kenji Matsuno, Hiroyuki Miyachi

Faculty of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

6 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 (NH_β). NMR, UV/vis, and circular dichroism measurements indicated that the conformation of these compounds is fixed by intramolecular interaction of CF₃ with NH_β to form a six-membered ring.

Original language	English
Pages (from-to)	6915-6918
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2014.10.107
Publication status	Published - Dec 10 2014

Keywords

Amino acid
Aziridine
Intramolecular interaction
Trifluoromethyl group

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2014.10.107

Cite this

@article{c70829efba644831a92114519ec26907,

title = "Synthesis of β-amino-α-trifluoromethyl-α-amino acids exhibiting intramolecular interaction of CF3 with NHβ",

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.",

keywords = "Amino acid, Aziridine, Intramolecular interaction, Trifluoromethyl group",

author = "Minoru Waki and Toshimasa Katagiri and Kenji Matsuno and Hiroyuki Miyachi",

note = "Funding Information: This work was supported by Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology, Japan . Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

year = "2014",

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day = "10",

doi = "10.1016/j.tetlet.2014.10.107",

language = "English",

volume = "55",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of β-amino-α-trifluoromethyl-α-amino acids exhibiting intramolecular interaction of CF3 with NHβ

AU - Waki, Minoru

AU - Katagiri, Toshimasa

AU - Matsuno, Kenji

AU - Miyachi, Hiroyuki

N1 - Funding Information: This work was supported by Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology, Japan . Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2014/12/10

Y1 - 2014/12/10

N2 - 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.

AB - 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.

KW - Amino acid

KW - Aziridine

KW - Intramolecular interaction

KW - Trifluoromethyl group

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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