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Axial chirality in biaryl N , N ‐dialkylaminopyridine derivatives bearing an internal carboxy group
Author(s) -
Nishino Reiko,
Hamada Shohei,
Elboray Elghareeb E.,
Ueda Yoshihiro,
Kawabata Takeo,
Furuta Takumi
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.23207
Subject(s) - racemization , chemistry , chirality (physics) , circular dichroism , axial chirality , enantiomer , nucleophile , stereochemistry , kinetic resolution , derivative (finance) , group (periodic table) , optically active , asymmetric induction , catalysis , crystallography , enantioselective synthesis , organic chemistry , chiral symmetry , physics , quantum mechanics , financial economics , nambu–jona lasinio model , economics , quark
Abstract Axial chirality in N , N ‐dimethylaminopyridines as well as N , N ‐dipropylaminopyridines bearing an internal carboxy group were evaluated based on their racemization barriers and circular dichroism spectra. The half‐life of racemization of N , N ‐dipropylaminopyridine derivative 2 was estimated to be 19.7 days at 20°C. Its enantiomers isolated as optically active forms showed positive‐negative and negative‐positive Cotton effects for (+)‐ 2 and (−)‐ 2 , respectively, from 310 to 210 nm. Furthermore, (−)‐ 2 was applied as a chiral nucleophilic catalyst and exhibited asymmetric induction in acylative kinetic resolution of 1‐(1‐naphthyl)ethane‐1‐ol.