NDLI: From substituent effects to applications: enhancing the optical response of a four-component assembly for reporting ee values

Content Provider	Royal Society of Chemistry (RSC)
Author	Lin, Chung-Yon Anslyn, Eric V. Giuliano, Michael W. Ellis, Bryan D. Miller, Scott J.
Copyright Year	2016
Abstract	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 determination. 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.
Starting Page	4085
Ending Page	4090
Page Count	6
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	7
Issue Number	7
Journal	Chemical Science
DOI	10.1039/c5sc04629g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Chirality Enantiomer High-throughput screening Dynamic range Alcohol Steric effects Substituent High-performance liquid chromatography
Content Type	Text
Resource Type	Article
Subject	Chemistry

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From substituent effects to applications: enhancing the optical response of a four-component assembly for reporting ee values† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc04629g

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