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Molecules 2016, 21(6), 788; doi:10.3390/molecules21060788

Aldol Reactions of Axially Chiral 5-Methyl-2-(o-aryl)imino-3-(o-aryl)-thiazolidine-4-ones

Chemistry Department, Bogazici University, Bebek, 34342 İstanbul, Turkey
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Author to whom correspondence should be addressed.
Academic Editor: Yoshio Okamoto
Received: 21 April 2016 / Revised: 6 June 2016 / Accepted: 8 June 2016 / Published: 18 June 2016
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Abstract

Axially chiral 5-methyl-2-(o-aryl)imino-3-(o-aryl)-thiazolidine-4-ones have been subjected to aldol reactions with benzaldehyde to produce secondary carbinols which have been found to be separable by HPLC on a chiral stationary phase. Based on the reaction done on a single enantiomer resolved via a chromatographic separation from a racemic mixture of 5-methyl-2-(α-naphthyl)imino-3-(α-naphthyl)-thiazolidine-4-one by HPLC on a chiral stationary phase, the aldol reaction was shown to proceed via an enolate intermediate. The axially chiral enolate of the thiazolidine-4-one was found to shield one face of the heterocyclic ring rendering face selectivity with respect to the enolate. The selectivities observed at C-5 of the ring varied from none to 11.5:1 depending on the size of the ortho substituent. Although the aldol reaction proceeded with a lack of face selectivity with respect to benzaldehyde, recrystallization returned highly diastereomerically enriched products. View Full-Text
Keywords: chromatographic separations on a chiral stationary phase; axial chirality; aldol reactions of thiazolidine-4-ones chromatographic separations on a chiral stationary phase; axial chirality; aldol reactions of thiazolidine-4-ones
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Erol Gunal, S.; Dogan, I. Aldol Reactions of Axially Chiral 5-Methyl-2-(o-aryl)imino-3-(o-aryl)-thiazolidine-4-ones. Molecules 2016, 21, 788.

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