Yes / t-BuOK-mediated rearrangement of 1,3-ketoesters with 2-(azidomethyl) aromatics in a two-step, one-pot telescoped sequence affords β-enaminoketoesters in moderate to good yields. A novel pathway is proposed in which the umpolung of the azide is achieved from electrophilicity to nucleophilicity via deprotonation and undergoes nucleophilic attack onto the 1,3-ketoester.
| Identifer | oai:union.ndltd.org:BRADFORD/oai:bradscholars.brad.ac.uk:10454/17851 |
| Date | 2014 July 1923 |
| Creators | Yan, Z., Wu, Na, Liang, D., Wang, H., Pan, Y. |
| Source Sets | Bradford Scholars |
| Language | English |
| Detected Language | English |
| Type | Letter, Accepted manuscript |
| Rights | © 2014 ACS. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer-review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/ol501930f., Unspecified |
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