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Stereochemical analysis of chiral amines, diamines, and amino alcohols: Practical chiroptical sensing based on dynamic covalent chemistry
Author(s) -
Hassan Diandra S.,
Thanzeel F. Yushra,
Wolf Christian
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23185
Subject(s) - chemistry , circular dichroism , enantiomer , chirality (physics) , absolute configuration , analyte , enantiomeric excess , covalent bond , substrate (aquarium) , schiff base , optical rotation , chloroform , organic chemistry , enantioselective synthesis , combinatorial chemistry , stereochemistry , chromatography , catalysis , chiral symmetry breaking , physics , oceanography , quantum mechanics , geology , nambu–jona lasinio model , quark
Practical chiroptical sensing with a small group of commercially available aromatic aldehydes is demonstrated. Schiff base formation between the electron‐deficient 2,4‐dinitrobenzaldehyde probe and either primary amines, diamines, or amino alcohols proceeds smoothly in chloroform at room temperature and is completed in the presence of molecular sieves within 2.5 hours. The substrate binding coincides with a distinct circular dichroism signal induction at approximately 330 nm, which can be correlated to the absolute configuration and enantiomeric composition of the analyte. The usefulness of this sensing method is highlighted with the successful sensing of 18 aliphatic and aromatic amines and amino alcohols and five examples showing quantitative % ee determination with good accuracy.