Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols
DOI: 10.14469/hpc/5977 Metadata
Created: 2019-07-26 10:51
Last modified: 2021-02-03 18:05
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: Alan Spivey Co-author: Andrea Salzano Co-author: Christian Nielsen Co-author: Jordi Bures Co-author: Riccardo Di Sanza Co-author: Xavier Companyó
Description
Downstream intermediates are crucial for the reactivity and selectivity of aminocatalytic reactions. We present an analysis of the stereopreference in aminocatalytic downstream intermediates, which reveals an inconspicuous mechanism of chiral recognition between the catalyst and the rest of the molecule. We delineate a stereoelectronic model to rationalize the mode of chiral transmission. We also exploit it for the resolution of chiral lactols relevant in organic synthesis as well as in the flavor and fragrance industry.
Files
| Filename | Size | Type | Description |
|---|---|---|---|
| spreadsheet.csv | 37KB | text/csv | Crystal structure search query results |
| search.qry | 6KB | application/octet-stream | Conquest search query |
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/6273 | FAIR Data table. Computed relative free energies of cyclic chiral lactols |
| 10.14469/hpc/5100 | Computed relative free energies of cyclic chiral lactols |
| 10.14469/hpc/6665 | NMR Spectra for Diastereopreference of intermediates in aminocatalysis: understanding and application to the chiral resolution of lactols |
Associated DOIs
| Current dataset ... | DOI | Description |
|---|---|---|
| References | 10.1021/acs.joc.0c02998 | Published article: Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols |