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
收藏
页数：6
相关论文
共 50 条
  • [11] Crystallization-Induced Emission of Azobenzene Derivatives
    Yamauchi, Mitsuaki
    Yokoyama, Kosuke
    Aratani, Naoki
    Yamada, Hiroko
    Masuo, Sadahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (40) : 14173 - 14178
  • [12] Asymmetric synthesis of N-substituted alpha-aminobenzlactam via crystallization-induced asymmetric transformation of covalent diastereomer
    Shieh, WC
    Carlson, JA
    Zaunius, GM
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23): : 8271 - 8272
  • [13] Developing processes for crystallization-induced asymmetric transformation
    Anderson, NG
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (06) : 800 - 813
  • [14] Crystallization-induced asymmetric transformation of a tertiary phosphine
    Vedejs, E
    Donde, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08): : 2337 - 2343
  • [15] Preparation of chiral 3-oxocycloalkanecarbonitrile and its derivatives by crystallization-induced diastereomer transformation of ketals with chiral 1,2-diphenylethane-1,2-diol
    Yamashita, Yohei
    Maki, Daisuke
    Sakurai, Shiho
    Fuse, Takumi
    Matsumoto, Shoji
    Akazome, Motohiro
    RSC ADVANCES, 2018, 8 (57): : 32601 - 32609
  • [16] Practical Manufacturing Process for Baloxavir Marboxil: Effective Selection and Replacement of Protective Group toward Enhancement of Crystallization-Induced Diastereomer Transformation
    Fukui, Nobuaki
    Shibahara, Setsuya
    Maki, Toshikatsu
    Ueno, Tatsuhiko
    Yanagisawa, Shuichi
    Okamoto, Kazuya
    Tanimoto, Emi
    Ohara, Takafumi
    Yasukata, Tatsuro
    Tsuritani, Takayuki
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2024, 28 (06) : 2139 - 2149
  • [17] Progress of Crystallization-Induced Asymmetric Transformation in Resolution of Chiral Compounds
    Xiong, Wenyue
    Wang, Hong
    Yi, Yu
    Mei, Jianfeng
    Ying, Guoqing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (07) : 951 - 957
  • [18] Crystallization-induced light-emission enhancement of diphenylmethane derivatives
    Guieu, Samuel
    Rocha, Joao
    Silva, Artur M. S.
    TETRAHEDRON, 2013, 69 (44) : 9329 - 9334
  • [19] Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation
    Kanomata, Nobuhiro
    Mishima, Gou
    Onozato, Jun
    TETRAHEDRON LETTERS, 2009, 50 (04) : 409 - 412
  • [20] Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base
    Zanetti, Andrea
    Chaumont-Olive, Pauline
    Schwertz, Geoffrey
    de Oliveira, Marllon Nascimento
    Fernandez, Mario Andres Gomez
    Amara, Zacharias
    Cossy, Janine
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2020, 24 (05) : 850 - 855
12345