烯丙基重排
磷化氢
区域选择性
对映选择合成
催化作用
化学
布朗斯特德-洛瑞酸碱理论
组合化学
二烯
镍
有机化学
天然橡胶
作者
Jiao Long,Yuqiang Li,Weining Zhao,Guoyin Yin
出处
期刊:Chemical Science
[The Royal Society of Chemistry]
日期:2022-01-01
卷期号:13 (5): 1390-1397
被引量:30
摘要
While chiral allylic organophosphorus compounds are widely utilized in asymmetric catalysis and for accessing bioactive molecules, their synthetic methods are still very limited. We report the development of asymmetric nickel/Brønsted acid dual-catalyzed hydrophosphinylation of 1,3-dienes with phosphine oxides. This reaction is characterized by an inexpensive chiral catalyst, broad substrate scope, and high regio- and enantioselectivity. This study allows the construction of chiral allylic phosphine oxides in a highly economic and efficient manner. Preliminary mechanistic investigations suggest that the 1,3-diene insertion into the chiral Ni-H species is a highly regioselective process and the formation of the chiral C-P bond is an irreversible step.
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