Phosphoric Acid Catalyzed Asymmetric 1,6-Conjugate Addition of Thioacetic Acid to para -Quinone Methides
| Autor: | Zhi-Pei Zhang, Xin Li, Jin-Pei Cheng, Nan Dong, Xiao-Song Xue |
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| Rok vydání: | 2015 |
| Předmět: |
Proton
010405 organic chemistry Enantioselective synthesis chemistry.chemical_element General Medicine General Chemistry 010402 general chemistry 01 natural sciences Sulfur Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Organocatalysis Organic chemistry Thioacetic acid Phosphoric acid Conjugate |
| Zdroj: | Angewandte Chemie International Edition. 55:1460-1464 |
| ISSN: | 1433-7851 |
| Popis: | An asymmetric 1,6-conjugate addition of thioacetic acid with para-quinone methides has been developed by using chiral phosphoric acid catalysis in the presence of water. A series of sulfur-containing compounds were thus obtained in high yields with good to excellent enantioselectivities. Theoretical studies indicated that the water-bridged proton transfer is a potentially favorable reaction pathway. An unprecedented O-H⋅⋅⋅π interaction between water and the aromatic nucleus of chiral phosphoric acid was discovered to contribute significantly to the stereocontrol in the catalysis. |
| Databáze: | OpenAIRE |
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