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European Journal of Organic Chemistry

European Journal of Organic Chemistry

IF: 2.5
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Deracemization of Quinolonecarboxamides by Dynamic Crystalline Salt Formation and Asymmetric Photoreaction by Using the Frozen Chirality

Published:9 September 2014 DOI: 10.1002/ejoc.201403056
Fumitoshi Yagishita, Naoya Takagishi, Hiroki Ishikawa, Yoshio Kasashima, Takashi Mino, Masami Sakamoto

Abstract

An asymmetric photoreaction by using chirality provided by dynamic chiral salt formation was demonstrated. Crystallization of racemic 2-quinolone-3-carboxamide and 2-quinolone-4-carboxamide with enantiopure L-dibenzoyltartaric acid led to deracemization and gave high diastereomeric excess values of the crystalline salts in almost quantitative yield. The axial chirality was retained for a long period of time after the salts were dissolved in cooled solvent. The frozen chirality derived from the chiral salts was effectively transferred to the products by using a typical [2+2] photocycloaddition reaction with alkenes.

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Dibenzoyl-L-tartaric acid 2743-38-6 C18H14O8 634 suppliers $10.00-$3418.80
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