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.

引用

页数：6

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