Abstract
(Chemical Equation Presented) Copper-catalyzed reactions of carbonyl-ene-nitriles with carbon nucleophiles, such as aromatics and ketones, afforded pyrrolin-2-ones (γ-lactam) in excellent yield. The reaction mechanism involves addition reactions with a ketimine moiety of the 2-aza-2,4-cyclopentadienone intermediate, which is formed via hydration of a nitrile moiety followed by dehydrative cyclization.
| Original language | English |
|---|---|
| Pages (from-to) | 9174-9176 |
| Number of pages | 3 |
| Journal | Journal of Organic Chemistry |
| Volume | 73 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - Nov 21 2008 |
ASJC Scopus subject areas
- Organic Chemistry
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Murai, M., Miki, K., & Ohe, K. (2008). Copper-catalyzed addition reactions of aromatics and ketones to 2-aza-2,4-cyclopentadienone: Facile and efficient transformation of carbonyl-ene-nitriles to 1H-pyrrolin-2(5H)-ones. Journal of Organic Chemistry, 73(22), 9174-9176. https://doi.org/10.1021/jo801776v