Citation: Yun-Xia Li, Yi-Lin Sheng, Bi-Song Zhang. A novel Ireland-Claisen rearrangement/Diels-Alder tandem reaction of propargylic acrylates with acyclic dienophiles[J]. Chinese Chemical Letters, ;2013, 24(2): 137-139. shu

A novel Ireland-Claisen rearrangement/Diels-Alder tandem reaction of propargylic acrylates with acyclic dienophiles

1.
College of Pharmaceutics and Material Engineering, Jinhua College of Profession and Technology, Jinhua 321007, China

Corresponding author: Yun-Xia Li,
Received Date: 18 October 2012
Available Online: 21 December 2012
Fund Project: The authors gratefully acknowledge the financial support from the Education Department of Zhejiang Province (No. Y201120940). (No. Y201120940)

A novel DABCO-catalyzed Ireland-Claisen rearrangement/Diels-Alder tandem reaction of propargylic acrylates 3 with dienophiles 4 was developed in the presence of an excess TMSCl and DBU with 1% hydroquinone as polymerization inhibitor in acetonitrile at refluxing temperature under air. This protocol gave cyclic a,b-unsaturated carboxylic acids 5 with complete regioselectivity.
- Ireland-Claisen rearrangement,
- Diels-Alder reaction,
- Tandem reaction,
- Propargylic acrylates
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沈阳化工大学材料科学与工程学院沈阳 110142