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Rational Design of Simple Organocatalysts for the $HSiCl_{3}$ Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline
| Content Provider | MDPI |
|---|---|
| Author | Mar, ía Maciá Vicente, Martí-Centelles Eduardo, García-Verdugo Porcar, Raúl Burguete, Maria Isabel Luis, Santiago V. |
| Copyright Year | 2021 |
| Description | Prolinamides are well-known organocatalysts for the $HSiCl_{3}$ reduction of imines; however, custom design of catalysts is based on trial-and-error experiments. In this work, we have used a combination of computational calculations and experimental work, including kinetic analyses, to properly understand this process and to design optimized catalysts for the benchmark (E)-N-(1-phenylethylidene)aniline. The best results have been obtained with the amide derived from 4-methoxyaniline and the N-pivaloyl protected proline, for which the catalyzed process is almost 600 times faster than the uncatalyzed one. Mechanistic studies reveal that the formation of the component supramolecular complex $catalyst-HSiCl_{3}$-substrate, involving hydrogen bonding breaking and costly conformational changes in the prolinamide, is an important step in the overall process. |
| Starting Page | 6963 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules26226963 |
| Journal | Molecules |
| Issue Number | 22 |
| Volume Number | 26 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-11-18 |
| Access Restriction | Open |
| Subject Keyword | Molecules Organocatalysis Asymmetric Catalysis Trichlorosilane Imine Reduction Mechanistic Studies |
| Content Type | Text |
| Resource Type | Article |
