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One-Pot Stepwise Approach to β-Enaminoketoesters through “Masked” 1,3-Aza-Dipoles
Yan, Z. Liang, D. Wang, H. Pan, Y.
Yan, Z.
Liang, D.
Wang, H.
Pan, Y.
Publication Date
01/08/2014
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© 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.
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Abstract
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.
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Accepted manuscript
Citation
Yan Z, Wu N, Liang D et al (2014) One-Pot Stepwise Approach to β-Enaminoketoesters through “Masked” 1,3-Aza-Dipoles. Organic Letters. 16(15): 4048-4051.
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Letter