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3685767 
Journal Article 
Solvent-induced dual chirality switching in the optical resolution of tropic acid via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol 
Kodama, K; Kurozumi, N; Shitara, H; Hirose, T 
2014 
1 
Tetrahedron
ISSN: 0040-4020 
Tetrahedron 
70 
43 
7923-7928 
WOS:000343344500013 
Abstract: SOLVENT*-induced chirality switching in the optical resolution of racemic tropic acid (TA) with (1R,2S)-2-amino-1,2-diphenylethanol has been demonstrated. Recrystallization of the diastereomeric salt mixture from i-PrOH or EtOH afforded the (S)-TA salt, while the (R)-TA salt was deposited from 1,4-dioxane and water-enriched alcohol solutions. Dual chirality switching was achieved by using two different types of SOLVENT*s. The X-ray crystal structures of both diastereomeric salts showed that incorporation of the crystallization SOLVENT* played a crucial role in stabilizing each diastereomeric salt crystal. The mechanism of chirality switching has been discussed on the basis of the relative stability of the salt, as deduced from their structures. (C) 2014 Elsevier Ltd. All rights reserved. ds: Chemistry cument Delivery No.: AR1KQ e field[29]: 1,4-Dioxane 
Optical resolution; Chirality; Inclusion crystal; Solvent effect; beta-Hydroxycarboxylic acid