对称化
对映选择合成
钯
催化作用
化学
卤化
反应性(心理学)
阿托品
有机化学
组合化学
医学
病理
替代医学
作者
Linxi Yao,Alemayehu Gashaw Woldegiorgis,Shilin Huang,Yongtao Wang,Xufeng Lin
标识
DOI:10.1002/chem.202203051
摘要
The discovery of enantioselective desymmetrization reactions to provide practical synthesis of enantio-enriched atropisomeric biaryls is a challenging topic in the field of asymmetric catalysis. Herein, we report a highly enantioselective desymmetrization reaction for the synthesis of axially chiral biaryl N-oxides by atroposelective C-H iodination by using Pd(II) coordinated by N-benzoyl-l-phenylalanine as a chiral catalyst at room temperature. A broad range of products were obtained in high yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee). The products could be synthesized in gram scale, one of which was proved to be a powerful organocatalyst in asymmetric allylation reaction. Mechanistic evidence as well as DFT calculations point towards the factors that lead to high reactivity and excellent enantiocontrol in this reaction.
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