Effect of a substituent on an aromatic group in diastereomeric resolution

Kazushi Kinbara; Koji Oishi; Yoshiko Harada; Kazuhiko Saigo

doi:10.1016/S0040-4020(00)00472-5

Effect of a substituent on an aromatic group in diastereomeric resolution

Kazushi Kinbara, Koji Oishi, Yoshiko Harada, Kazuhiko Saigo

Institute of Multidisciplinary Research for Advanced Materials (IMRAM)

Research output: Contribution to journal › Article

40 Citations (Scopus)

Abstract

The diastereomeric resolution of p-substituted 1-arylethylamines by enantiopure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic group of the racemic amines would affect the efficiency of resolution. As a result, it was found that 1-arylethylamines having an electron-withdrawing substituent could be efficiently resolved by (S)-2, while the amines having an electron-donating group could not. The crystal structures of the less- and more-soluble salts, and the molecular orbital calculations of the ammonium cations indicated that the p-substituted electron-withdrawing group enhanced the positive charge on the meta-hydrogen of the aromatic group of the ammonium cations, which is favorable for the formation of a CH···π interaction in crystal. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6651-6655
Number of pages	5
Journal	Tetrahedron
Volume	56
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4020(00)00472-5
Publication status	Published - 2000 Jan 1

Keywords

Chiral discrimination
Crystal engineering
Diastereomer method

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Kinbara, K., Oishi, K., Harada, Y., & Saigo, K. (2000). Effect of a substituent on an aromatic group in diastereomeric resolution. Tetrahedron, 56(36), 6651-6655. https://doi.org/10.1016/S0040-4020(00)00472-5

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AU - Kinbara, Kazushi

AU - Oishi, Koji

AU - Harada, Yoshiko

AU - Saigo, Kazuhiko

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N2 - The diastereomeric resolution of p-substituted 1-arylethylamines by enantiopure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic group of the racemic amines would affect the efficiency of resolution. As a result, it was found that 1-arylethylamines having an electron-withdrawing substituent could be efficiently resolved by (S)-2, while the amines having an electron-donating group could not. The crystal structures of the less- and more-soluble salts, and the molecular orbital calculations of the ammonium cations indicated that the p-substituted electron-withdrawing group enhanced the positive charge on the meta-hydrogen of the aromatic group of the ammonium cations, which is favorable for the formation of a CH···π interaction in crystal. (C) 2000 Elsevier Science Ltd.

AB - The diastereomeric resolution of p-substituted 1-arylethylamines by enantiopure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic group of the racemic amines would affect the efficiency of resolution. As a result, it was found that 1-arylethylamines having an electron-withdrawing substituent could be efficiently resolved by (S)-2, while the amines having an electron-donating group could not. The crystal structures of the less- and more-soluble salts, and the molecular orbital calculations of the ammonium cations indicated that the p-substituted electron-withdrawing group enhanced the positive charge on the meta-hydrogen of the aromatic group of the ammonium cations, which is favorable for the formation of a CH···π interaction in crystal. (C) 2000 Elsevier Science Ltd.

KW - Chiral discrimination

KW - Crystal engineering

KW - Diastereomer method

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