Iminium Ion and N‑Hydroxyimide as the Surrogate Components in DEAD-Promoted Oxidative Ugi Variant
A practical metal-free oxidative Ugi-type three-component assembly has been achieved efficiently, employing a tertiary-amine-derived iminium ion as an imine surrogate, N-hydroxyimide as an acid surrogate, and DEAD as an oxidant. This dual-surrogate Ugi variant proceeded with a broad substrate scope...
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Veröffentlicht in: | Journal of organic chemistry 2018-11, Vol.83 (21), p.13121-13131 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A practical metal-free oxidative Ugi-type three-component assembly has been achieved efficiently, employing a tertiary-amine-derived iminium ion as an imine surrogate, N-hydroxyimide as an acid surrogate, and DEAD as an oxidant. This dual-surrogate Ugi variant proceeded with a broad substrate scope and desired functional group tolerance, leading to a wide range of N-alkyl-N-acyl aminophthalimide and N-alkyl-N-acylaminosuccinimide derivatives in good isolated yields. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b01868 |