|
|||||
|
|
First report of syn isomers in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid: factors influencing the syn-anti ratios |
|
| Authors: | Chhanda Mukhopadhyay Sunil RanaRay J Butcher Ann Marie Schmiedekamp |
| Institution: | a Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata-700 009, India b Department of Chemistry, Howard University, Washington DC 20059, USA c Division of Science and Engineering, Penn State University Abington, Abington, PA 19001, USA |
| Abstract: | This is the first report of the formation of a syn-diastereoisomer in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid via a one-pot, step-economic condensation of aromatic aldehydes, 1,3-dicarbonyl compounds and aromatic amines. DFT calculation shows that anti isomers are more stable compared to the syn. The syn-anti ratio of the products depends on the temperature and the nature of substitution on both the aromatic aldehydes and aromatic amines. Conditions for getting pure anti and pure syn compounds have been studied. |
| Keywords: | syn-Diastereoselectivity Highly functionalized piperidines Wet picric acid Room temperature Multicomponent reaction |
| 本文献已被 ScienceDirect 等数据库收录！ | |