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B(C6F5)3/Chiral Phosphoric Acid Catalyzed Ketimine‐ene Reaction of 2‐Aryl‐3H‐indol‐3‐ones and α‐Methylstyrenes
Angewandte Chemie International Edition ( IF 12.257 ) Pub Date : 2020-01-13 , DOI: 10.1002/anie.201915226
Xin Li; Qing-Xia Zhang; Yao Li; Jie Wang; Chen Yang; Cheng-Jun Liu; Jin-Pei Cheng

The enantioselective ketimine‐ene reaction represents one of the most challenging stereo‐controlled reaction type in organic synthesis. In this article, catalytic enantioselective ketimine‐ene reactions of 2‐aryl‐3 H ‐indol‐3‐ones with α‐methylstyrenes are achieved by utilizing a B(C 6 F 5 ) 3 /chiral phosphoric acid complex catalyst. These ketimine‐ene reactions proceed well with low catalyst loading (B(C 6 F 5 ) 3 /CPA = 2 mol%/ 2 mol%) under mild conditions, providing a rapid and facile access to a series of functionalized 2‐allyl‐indolin‐3‐ones with very good reactivities (up to 99% yield) and excellent enantioselectivities (up to 99% ee ). Theoretical calculations reveal enhancement of the acidity of chiral phosphoric acid by B(C 6 F 5 ) 3 significantly reduce the activation free energy barrier. And the collective favorable hydrogen bonding interactions, especially the enhanced N‐H•••O hydrogen bonding interaction differentiate the free energy between the transition states of CPA and B(C 6 F 5 ) 3 /CPA inducing the improvement of stereoselectivity.
更新日期:2020-01-14

 

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