Title
Axial chirality in biaryl N ,N ‐dialkylaminopyridine derivatives bearing an internal carboxy group
Author
Reiko Nishino, Shohei Hamada, Elghareeb E. Elboray, Yoshihiro Ueda, Takeo Kawabata, Takumi Furuta
Year
2020
Journal
Chirality, Volume32, Issue5 May 2020 Pages 588-593
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.
Keywords
axial chirality, circular dichroism acylative kinetic resolution, DMAP derivative