Possible Case of Halogen Bond-Driven Self-Disproportionation of Enantiomers (SDE) via Achiral Chromatography

被引：17

作者：

Terada, Shumpei ^{[1
]}

Hirai, Motohiro ^{[1
]}

Honzawa, Ayaka ^{[1
]}

Kitagawa, Osamu ^{[1
]}

Kamizela, Angelika ^{[2
]}

Wzorek, Alicja ^{[2
,3
]}

Soloshonok, Vadim A. ^{[3
,4
]}

机构：

[1] Shibaura Inst Technol, Dept Appl Chem, Kohto Ku, 3-7-5 Toyosu, Tokyo 1358548, Japan

[2] Jan Kochanowski Univ Kielce, Inst Chem, Swietokrzyska 15G, PL-25406 Kielce, Poland

[3] Univ Basque Country UPV EHU, Dept Organ Chem 1, Fac Chem, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain

[4] Univ Basque Country UPV EHU, JKERBASQUE, Basque Fdn Sci, Maria Diaz de Haro 3, Bilbao 48013, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 58期

关键词：

axially chiral compounds; enantiomeric purifications; halogen bonding; molecular chirality; self-disproportionation of enantiomers (SDE); CATALYTIC ENANTIOSELECTIVE SYNTHESIS; NON-RACEMIC MIXTURES; AXIALLY CHIRAL MEBROQUALONE; L-AMINO-ACIDS; SILICA-GEL; COLUMN CHROMATOGRAPHY; SYMMETRY-BREAKING; ASYMMETRIC CATALYSIS; PHASE CHROMATOGRAPHY; ENRICHMENT;

D O I：

10.1002/chem.201703308

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The major breakthrough reported in this work is the discovery of likely halogen bond-driven self-disproportionation of enantiomers (SDE). Taking into account that the halogen-bonding interactions can be rationally designed and can match, or even exceed, the strength of the more familiar hydrogen bond, this discovery clearly opens an unexpected new direction of research in the areas of molecular chirality and the SDE phenomenon.

引用

页码：14631 / 14638

页数：8

共 45 条

[41] Self-Complementary Nonlinear Optical-Phores Targeted to Halogen Bond-Driven Self-Assembly of Electro-Optic Materials
Cariati, Elena
Cavallo, Gabriella
Forni, Alessandra
Leem, Gyu
Metrangolo, Pierangelo
Meyer, Franck
Pilati, Tullio
Resnati, Giuseppe
Righetto, Stefania
Terraneo, Giancarlo
Tordin, Elisa
CRYSTAL GROWTH & DESIGN, 2011, 11 (12) : 5642 - 5648
[42] Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro)lactate via sublimation: Sublimation rates vs. enantiomeric composition
Yasumoto, Manabu
Ueki, Hisanori
Ono, Taizo
Katagiri, Toshimasa
Soloshonok, Vadim A.
JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (04) : 535 - 539
[43] FLUO 22-Self-disproportionation of enantiomers via AP-chromatography on a regular silica-gel
Soloshonok, Vadim A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[44] NMR spectral enantioresolution of spirobrassinin and 1-methoxyspirobrassinin enantiomers using (S)-(-)-ethyl lactate and modeling of spirobrassinin self-association for rationalization of its self-induced diastereomeric anisochromism (SIDA) and enantiomer self-disproportionation on achiral-phase chromatography (ESDAC) phenomena
Klika, Karel D.
Budovska, Mariana
Kutschy, Peter
JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (04) : 467 - 476
[45] NMR and molecular modeling of the dimeric self-association of the enantiomers of 1,1′-bi-2-naphthol and 1-phenyl-2,2,2-trifluoroethanol in the solution state and their relevance to enantiomer self-disproportionation on achiral-phase chromatography (ESDAC)
Nieminen, Ville
Murzin, Dmitry Yu.
Klika, Karel D.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (03) : 537 - 542

← 1 2 3 4 5 →