Chirality Sensing of Amines, Diamines, Amino Acids, Amino Alcohols, and α‑Hydroxy Acids with a Single Probe

A stereodynamic probe for determination of the absolute configuration and enantiomeric composition of chiral amines, diamines, amino alcohols, amino acids, and α-hydroxy carboxylic acids is described. The chirality sensing is based on spontaneous asymmetric transformation of the first kind with ster...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 135; no. 48; pp. 18052 - 18055
Main Authors Bentley, Keith W, Nam, Yea G, Murphy, Jaslynn M, Wolf, Christian
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.12.2013
Subjects
Amines - chemistry
Amino Acids - chemistry
Amino Alcohols - chemistry
Boron - chemistry
Coordination Complexes - chemistry
Diamines - chemistry
Hydroxy Acids - chemistry
Models, Molecular
Stereoisomerism
Zinc - chemistry
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Summary:A stereodynamic probe for determination of the absolute configuration and enantiomeric composition of chiral amines, diamines, amino alcohols, amino acids, and α-hydroxy carboxylic acids is described. The chirality sensing is based on spontaneous asymmetric transformation of the first kind with stereolabile binaphtholate boron and zinc complexes. The substrate binding and chiral amplification processes yield a distinctive chiroptical sensor output at high wavelength that can be used for rapid and accurate ee detection of minute sample amounts.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja410428b