Deracemization of Quinolonecarboxamides by Dynamic Crystalline Salt Formation and Asymmetric Photoreaction by Using the Frozen Chirality | Zendy

Yagishita Fumitoshi | Zendy; Takagishi Naoya | Zendy; Ishikawa Hiroki | Zendy; Kasashima Yoshio | Zendy; Mino Takashi | Zendy; Sakamoto Masami | Zendy

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

Author(s) -

Yagishita Fumitoshi,

Takagishi Naoya,

Ishikawa Hiroki,

Kasashima Yoshio,

Mino Takashi,

Sakamoto Masami

Publication year - 2014

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201403056

Subject(s) - chirality (physics) , enantiopure drug , chemistry , diastereomer , salt (chemistry) , axial chirality , yield (engineering) , crystallization , solvent , stereochemistry , organic chemistry , photochemistry , enantioselective synthesis , catalysis , chiral symmetry , thermodynamics , nambu–jona lasinio model , physics , quantum mechanics , quark

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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