Citation: Hong-Rui Zhang, Ji-Jun Xue, Rui Chen, Yu Tang, Ying Li. A bifunctional rosin-derived thiourea catalyzed asymmetric tandem reaction and its new mechanism[J]. Chinese Chemical Letters, ;2014, 25(05): 710-714. doi: 10.1016/j.cclet.2013.12.024 shu

A bifunctional rosin-derived thiourea catalyzed asymmetric tandem reaction and its new mechanism

1.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China

Corresponding author: Yu Tang, Ying Li,
Received Date: 6 November 2013
Available Online: 31 December 2013
Fund Project:

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.
- Organocatalysis,
- Diels-Alder reaction,
- Chiral thiourea,
- Tandem reaction
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