Organocatalytic synthesis of chiral allene catalyzed by chiral phosphoric acid via asymmetric 1,8-addition of indole imine methide: Mechanism and origin of enantioselectivity

Peng-Yu Liang,Shaoting Shi,Xin-Xin Xu,Hai-Rong Zhang,Zheng Che,Ka Lu,Chao-Xian Yan,Neng-Zhi Jin,Pan-Pan Zhou

Molecular Catalysis（2022）

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摘要

•The mechanisms for organocatalytic synthesis of chiral allene by racemic propargylic alcohol and 3-phenylindole were proposed.•Eight possible reaction pathways were found after the dehydration process.•The intermolecular interactions including HBs and π-π interactions play crucial roles in determining the enantioselectivity.

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关键词

Chiral phosphoric acid,Hydrogen bond,Enantioselectivity,Chiral allene,Organocatalytic reaction

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