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

共 50 条

[1] Crystallization-induced diastereomer transformations
Brands, Karel M. J.
Davies, Antony J.
CHEMICAL REVIEWS, 2006, 106 (07) : 2711 - 2733
[2] Total Synthesis of (±)-Azaspirene via Crystallization-induced Diastereomer Transformation
Hirasawa, Shun
Kurashima, Takashi
Hasegawa, Takahiro
Souma, Kazunori
Kanomata, Nobuhiro
CHEMISTRY LETTERS, 2022, 51 (10) : 985 - 988
[3] Highly Diastereoselective Synthesis of 2-Arylpyrrolidine Derivatives via the Crystallization-induced Diastereomer Transformation
Smolobochkin, Andrey, V
Gazizov, Almir S.
Voronina, Julia K.
Burilov, Alexander R.
Pudovik, Michail A.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (01)
[4] Enantioselective synthesis of (-)-tetrabenazine via continuous crystallization-induced diastereomer transformation
Kukor, Andrew J.
Depner, Noah
Cai, Isabelle
Tucker, John L.
Culhane, Jeffrey C.
Hein, Jason E.
CHEMICAL SCIENCE, 2022, 13 (36) : 10765 - 10772
[5] State of the Art in Crystallization-Induced Diastereomer Transformations
Kolarovic, Andrej
Jakubec, Pavol
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (17) : 4110 - 4158
[6] Enantiopurification of Mandelic Acid by Crystallization-Induced Diastereomer Transformation: An Experimental and Computational Study
Sherwood, John N.
Lerdwiriyanupap, Tharit
Nalaoh, Phattananawee
Bureekaew, Sareeya
Cedeno, Ruel
Promarak, Vinich
Flood, Adrian E.
CRYSTAL GROWTH & DESIGN, 2023, 23 (03) : 2001 - 2010
[7] Guided optimization of a crystallization-induced diastereomer transformation to access a key navoximod intermediate
Kukor, Andrew J.
St-Jean, Frederic
Stumpf, Andreas
Malig, Thomas C.
Piechowicz, Katarzyna A.
Kurita, Kenji
Hein, Jason E.
REACTION CHEMISTRY & ENGINEERING, 2023, 8 (06) : 1294 - 1299
[8] Crystallization-induced diastereomer transformation assists the diastereoselective synthesis of 4-nitroisoxazolidine scaffolds
Esteban, Alberto
Ortega, Pablo
Sanz, Francisca
Jambrina, Pablo G.
Diez, David
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (32) : 6582 - 6592
[9] Crystallization-Induced Diastereomer Transformation of α-Bromo α′-Sulfinyl Ketones. Diastereodivergent Synthesis of (+)-α-Conhydrine and (-)-β-Conhydrine
Grenet, Erwann
Geant, Pierre-Yves
Salom-Roig, Xavier J.
ORGANIC LETTERS, 2021, 23 (21) : 8539 - 8542
[10] Crystallization-induced diastereomer transformation of 2-quinolone-4-carboxamide followed by stereoselective intermolecular photocycloaddition reaction
Sakamoto, Masami
Sato, Naoto
Mino, Takashi
Kasashima, Yoshio
Fujita, Tsutomu
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (05) : 848 - 850

← 1 2 3 4 5 →