標題: | Palladium-Catalyzed alpha-Allylation of Secondary Nitroalkanes with Allylic Alcohols and Strategic Exploitation of Seebach's Reagent for the Total Synthesis of (+/-)-Adalinine |
作者: | Chang, Chieh-Yu Wu, Yen-Ku 應用化學系 Department of Applied Chemistry |
公開日期: | 1-六月-2018 |
摘要: | A method is reported for the catalytic direct coupling of allylic alcohols and nitroalkanes. the allylation process, the synergistic action of palladium complexes and titanium(IV) alkoxide facilitates the formation of nitronate and pi-allylpalladium intermediate. In the cases of reluctant allylations, typically with sterically demanding nitroalkanes, we found the addition of substoichiometric amount of DBU greatly facilitates the desired transformation. We also accomplished a total synthesis of (+/-)-adalinine through a homoallyl nitroalkane derived from Seebach's reagent. |
URI: | http://dx.doi.org/10.1021/acs.joc.8b00710 http://hdl.handle.net/11536/145091 |
ISSN: | 0022-3263 |
DOI: | 10.1021/acs.joc.8b00710 |
期刊: | JOURNAL OF ORGANIC CHEMISTRY |
Volume: | 83 |
起始頁: | 6217 |
結束頁: | 6224 |
顯示於類別: | 期刊論文 |