Crystallization-induced diastereomer transformation of thiohydantoin derivatives

被引：15
|
作者：
Uemura, Naohiro [1 ]
Yoshida, Yasushi [1 ,2 ]
Mino, Takashi [1 ,2 ]
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
来源：
TETRAHEDRON | 2020年 / 76卷 / 20期
关键词：
Crystallization-induced diastereomer transformation; Optically active thiohydantoin; Dynamic crystallization; Epimerization; Aminal; ASYMMETRIC TRANSFORMATION; AMINO-ACIDS; DERACEMIZATION; HYDANTOINS; RESOLUTION;
D O I：
10.1016/j.tet.2020.131166
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Crystallization-induced diastereomer transformation of valuable thiohydantoin derivatives was developed for the first time. Three thiohydantoins synthesized from three (R)-N-phenethylthioureas and benzoylformyl chloride were obtained as diasteromeric mixtures. These thiohydantoins have aminal carbons at the chiral center which could be epimerized via ring-opening and -closing reactions under suitable conditions. The suspension of the diastereomixture of thiohydantoins in a small amount of solvent selectively converged to crystals composed of a single diastereomer in a quantitative fashion. Stereoselective switching of diastereoselectivity by CIDT of one thiohydantoin was achieved with a suitable solvent. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：6
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