Synthesis of functionalized 3-isochromanones via metal-free intramolecular alkoxylation-initiated cascade cyclization
| Autor: | Yin Xu, Long-Wu Ye, Jin-Mei Zhou, Tong-Yi Zhai, Ying-Qi Zhang, Hao-Zhen Bu, Jia-Le Wang, Xin-Qi Zhu |
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| Rok vydání: | 2019 |
| Předmět: |
Reaction conditions
chemistry.chemical_classification 010405 organic chemistry Chemistry Alkene Substrate (chemistry) 010402 general chemistry 01 natural sciences Pollution Combinatorial chemistry 0104 chemical sciences Catalysis Metal free Cascade Intramolecular force Environmental Chemistry Alkoxylation |
| Zdroj: | Green Chemistry. 21:3023-3028 |
| ISSN: | 1463-9270 1463-9262 |
| DOI: | 10.1039/c9gc01030k |
| Popis: | A metal-free intramolecular alkoxylation-initiated cascade cyclization of allyl ether-tethered ynamides has been developed. Various highly functionalized 3-isochromanones can be obtained in generally good to excellent yields under mild reaction conditions. Moreover, this asymmetric cyclization has also been realized via a stereocontrolled [3,3] rearrangement by employing a traceless chiral directing group. In addition, an unexpected [1,3] O-to-C rearrangement is observed in the case of the ynamide substrate bearing a phenyl-substituted alkene, which is distinctively different from the related gold catalysis. |
| Databáze: | OpenAIRE |
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