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Chiral auxiliary recycling in continuous flow: automated recovery and reuse of Oppolzer's sultam† †Electronic supplementary information (ESI) available: Experimental details, details of flow reactor and equipment, characterization data of compounds. See DOI: 10.1039/c7sc05192a
| Content Provider | Semantic Scholar |
|---|---|
| Author | Sullivan, Ryan J. Newman, Stephen A. |
| Copyright Year | 2018 |
| Abstract | The telescoping of a three-stage, chiral auxiliary-mediated transformation in flow is described, including continuous separation of the product and auxiliary. The auxiliary can either be collected for later reuse, or directly fed back to the beginning of the process for recycling in real time, enabling each molecule of auxiliary to make multiple equivalents of chiral product and thus minimizing the step- and atom-economy issues associated with auxiliary-mediated synthesis. This concept is demonstrated for the asymmetric hydrogenation of olefins using Oppolzer's sultam, shortening the total reaction time >100 fold compared to batch, and demonstrating formal sub-stoichiometric auxiliary loading with respect to the process by automating auxiliary recycling within a closed loop. |
| Starting Page | 2130 |
| Ending Page | 2134 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c7sc05192a |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/c7/sc/c7sc05192a/c7sc05192a1.pdf |
| PubMed reference number | 29719686 |
| Alternate Webpage(s) | https://doi.org/10.1039/c7sc05192a |
| Journal | Medline |
| Volume Number | 9 |
| Journal | Chemical science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
