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

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[32] The self-disproportionation of enantiomers (SDE): The effect of scaling down, potential problems versus prospective applications, possible new occurrences, and unrealized opportunities?
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[33] Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions
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[36] Self-disproportionation of enantiomers of 3,3,3-trifluorolactic acid amides via sublimation
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[37] Rational application of self-disproportionation of enantiomers via sublimation-a novel methodological dimension for enantiomeric purifications
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[38] Self-disproportionation of enantiomers of heterocyclic compounds having a tertiary trifluoromethyl alcohol center on chromatography with a non-chiral system
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[39] Fluorinated azobenzenes with highly strained geometries for halogen bond-driven self-assembly in the solid state
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[40] Self-disproportionation of enantiomers of (R)-ethyl 3-(3,5-dinitrobenzamido)-4,4,4-trifluorobutanoate on achiral silica gel stationary phase
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