对映选择合成
烯丙基重排
催化作用
铜
化学
有机化学
组合化学
药物化学
作者
Ruinan Zhao,Shuang Deng,Rongkang Huang,Han‐Han Kong,Yuepeng Lu,Tingrui Yin,Jiaqiang Wang,Ying Li,Cuiju Zhu,Fangfang Pan,Xiaotian Qi,Hao Xu
标识
DOI:10.1021/acscatal.4c01756
摘要
Catalytic asymmetric dearomatization reactions of α-unsubstituted β-naphthols are very challenging due to the high energy barrier resulting from the loss of aromaticity. Herein, we describe an example of enantioselective catalytic dearomative spiroannulation with yne-allylic esters. The success of this reaction relied on the copper-catalyzed remote asymmetric strategy using yne-allylic esters as the bis-electrophilic reagents. This transformation features mild reaction conditions, broad functional group tolerance, and an extensive substrate scope, thereby facilitating the efficient construction of an array of enantioenriched naphthalene-2-one and spiroindolenine derivatives. Experimental studies and density functional theory calculations establish the reaction pathway and origin of stereoselectivity.
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