New Atropisomeric Amino Alcohol Ligands for Enantioselective Addition of Diethylzinc to Aldehydes |
| |
| Authors: | F Faigl SZ Deák ZS Erdélyi T Holczbauer M Czugler M Nyerges B Mátravölgyi |
| |
| Institution: | 1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary;2. MTA‐BME Organic Chemical Technology Research Group, Hungarian Academy of Sciences, Budapest, Hungary;3. Institute of Structural Chemistry, Hungarian Academy of Sciences, Budapest, Hungary;4. Servier Research Institute of Medicinal Chemistry, Budapest, Hungary |
| |
| Abstract: | Efficient synthesis of several new atropisomeric amino alcohols having 1‐phenyl‐1H‐pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single‐crystal X‐ray measurement. The consequences of the size of the N‐substituents on enantioinduction were examined by employing the enantioselective catalytic addition of diethylzinc to a series of substituted benzaldehydes (yields 91–97%, up to 85% enantiomeric excess). The special effect of the ortho methoxy group of the substrate on the enantioinduction is also interpreted. Chirality 27:216–222, 2015. © 2014 Wiley Periodicals, Inc. |
| |
| Keywords: | amino alcohol selective hydrolysis axial chirality asymmetric catalysis aromatic aldehyde |
|
|
