Axial chirality in biaryl N,N-dialkylaminopyridine derivatives bearing an internal carboxy group |
| |
| Authors: | Reiko Nishino Shohei Hamada Elghareeb E. Elboray Yoshihiro Ueda Takeo Kawabata Takumi Furuta |
| |
| Affiliation: | 1. Institute for Chemical Research, Kyoto University, Uji, Japan;2. Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Kyoto, Japan;3. Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Kyoto, Japan Chemistry Department, Faculty of Science, South Valley University, Qena, Egypt |
| |
| 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 |
|
|
