From substituent effects to applications: enhancing the optical response of a four-component assembly for reporting ee values
| Autor: | Bryan D. Ellis, Michael W. Giuliano, Chung-Yon Lin, Scott J. Miller, Eric V. Anslyn |
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| Rok vydání: | 2016 |
| Předmět: |
Steric effects
Hplc analysis Four component 010405 organic chemistry Stereochemistry Chemistry Calibration curve Substituent Alcohol General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Article 0104 chemical sciences Catalysis chemistry.chemical_compound Enantiopure drug |
| Zdroj: | Chemical Science. 7:4085-4090 |
| ISSN: | 2041-6539 2041-6520 |
| DOI: | 10.1039/c5sc04629g |
| Popis: | High-throughput screening for asymmetric catalysts has stimulated an interest in optically-based enantiomeric-excess (ee) sensors, primarily for their improved time and cost efficiency when compared to the standard HPLC analysis. We present herein substituent-effect studies on a recently reported Zn(II) multicomponent assembly that is used for chiral, secondary alcohol ee detemination. The systematic altering of assemblies formed from select substituted pyridyl ligands pointed to the conclusion that steric effects dominate the mode of interaction at the pyridyl 3- and 6- positions. From these results we identified a new Zn(II)-centered multicomponent assembly with a higher dynamic range than previously reported. Calibration curves of the CD signals resulting from the new assembly led to an ee assay with a 1.7% error. To further the utility of the new assembly, a correlation was developed between alcohol substituent size to the respective enantiopure CD value. |
| Databáze: | OpenAIRE |
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