A bifunctional rosin-derived thiourea catalyzed asymmetric tandem reaction and its new mechanism |
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| Authors: | Hong-Rui Zhang Ji-Jun Xue Rui Chen Yu Tang Ying Li |
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| Institution: | State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China |
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| 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. |
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| Keywords: | Organocatalysis Diels–Alder reaction Chiral thiourea Tandem reaction |
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