烯丙基重排
铱
异构化
化学
催化作用
重排反应
烯烃
酒
卡罗尔重排
重排
氢化物
药物化学
光化学
组合化学
西格玛反应
立体化学
有机化学
氢
作者
Fēi Li,Yicong Luo,Xuejie Zhu,Yong Ye,Qianjia Yuan,Wanbin Zhang
标识
DOI:10.1002/chem.202300027
摘要
The allylic alcohol structural motif is prevalent in many important molecules and valuable building blocks. The rearrangement reaction is one of the most important transformations, however there are only a few reports for the 1,3-rearrangement of allylic alcohols. Herein, a 1,3-rearrangement of allylic alcohols catalyzed by an Ir(III) dihydride complex is described. This reaction could provide the corresponding less accessible allylic alcohols regio- and stereoselectively from readily available E/Z mixtures of the substrates. Furthermore, a tandem alkene isomerization followed by 1,3-rearrangement of homoallylic alcohols was also realized. In addition, this rearrangement reaction could be used to synthesize the natural product Navenone B. Mechanistic investigation indicated that the reaction pathway involved a π-allyl-Ir(V) intermediate and that the dihydride in the iridium catalyst acts as a hydrogen switch to modulate the valence of the iridium center.
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