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