| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1257402 | Chinese Chemical Letters | 2014 | 5 Pages |
A direct asymmetric tandem reaction of α-nitro ketones with β,γ-unsaturated α-ketoesters was found to be catalyzed by a bifunctional rosin-derived thiourea and gave 5-nitro-2-actoxyl-2-pentenates in excellent ee values and yields, a much better result than previously reported. Furthermore, through theoretical analysis, literature research and experimental verifications, a new mechanism involving an inverse-electron-demand Diels–Alder (IEDDAR) and a retro-Henry reaction was proposed.
Graphical abstract. A direct asymmetric tandem reaction of α-nitro ketones with β,γ-unsaturated α-ketoesters was found to be catalyzed by a bifunctional rosin-derived thiourea and gave 5-nitro-2-actoxyl-2-pentenates in excellent ee values and yields, a much better result than previously reported. Furthermore, through theoretical analysis, literature research and experimental verifications, a new mechanism involving an inverse-electron-demand Diels–Alder (IEDDAR) and a retro-Henry reaction was proposed.Figure optionsDownload full-size imageDownload as PowerPoint slide
