Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization

被引：7
|
作者：
Ishikawa, Hiroki [1 ]
Uemura, Naohiro [1 ]
Saito, Rei [1 ]
Yoshida, Yasushi [1 ,2 ]
Mino, Takashi [1 ,2 ]
Kasashima, Yoshio [3 ]
Sakamoto, Masami [1 ,2 ]
机构：
[1] Chiba Univ, Grad Sch Engn, Dept Appl Chem & Biotechnol, Inage Ku, Yayoi Cho, Chiba 2638522, Japan
[2] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, Yayoi Cho, Chiba 2638522, Japan
[3] Chiba Inst Technol, Fac Creat Engn, Educ Ctr, Narashino, Chiba 2750023, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 41期
关键词：
chiral symmetry breaking; deracemization; dynamic crystallization; spirooxazines; spiropyrans; INDUCED ASYMMETRIC TRANSFORMATION; THERMAL RACEMIZATION; RESOLUTION; IMPURITIES; DERACEMIZATION; SUBSTITUENT; GENERALITY; SYSTEMS; FORMS; RULE;
D O I：
10.1002/chem.201901889
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor-diffusion crystallization or attrition-enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single-crystal X-ray analysis and each enantiomorphic crystal was correlated with its solid-state circular dichroism (CD) spectrum.
引用
收藏
页码：9758 / 9763
页数：6
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