阿托品
对映选择合成
区域选择性
化学
立体选择性
键裂
异喹啉
组合化学
立体化学
催化作用
有机化学
作者
Ruixian Deng,Puyang Dong,Jimeng Ge,Wenjing Zhang,Xiaoping Xue,Longhui Duan,Linlin Shi,Zhenhua Gu
标识
DOI:10.1002/ange.202402231
摘要
Abstract The development of new methods for regio‐ and stereoselective activation of C−O bonds in ethers holds significant promise for synthetic chemistry, offering advantages in terms of environmental sustainability and economic efficiency. Moreover, the C−N atropisomers represent a fascinating and crucial chiral system, extensively found in natural products, pharmaceutical leads, and the frameworks of advanced materials. In this work, we have introduced a nickel‐catalyzed regio‐ and enantioselective carbon‐oxygen arylation reaction for atroposelective synthesis of N ‐arylisoquinoline‐1,3(2 H ,4 H )‐diones. The high regioselectivity of C−O cleavage benefits from the high stability of the in situ formed (amido)ethenolate via oxidative addition. Additionally, the self‐activation of the aryl C−O bond facilitates the reaction under mild conditions, leading to outstanding enantioselectivities. The diverse post‐functionalizations of the axially chiral isoquinoline‐1,3(2 H ,4 H )‐diones further highlighted the utility of this protocol in preparing valuable C−N atropisomers, including the chiral phosphine ligands.
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