Electrochemical Reductive Bimolecular Cycloaddition of 2-Arylideneindane-1,3-diones for the Synthesis of
Luchao Li1, Binyan Xu1, Chenglong Jia1
1College of Biotechnology and Pharmaceutical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, China.
Abstract:
An electrochemical reductive bimolecular cycloaddition of 2-arylideneindane-1,3-diones has been reported for the synthesis of spirocyclopentanole indane-1,3-diones bearing five contiguous stereocenters with vicinal tetrasubstituted stereocenters, especially involving a quaternary carbon center, in moderate to good yields and excellent diastereoselectivities. The present protocol features mild reaction conditions, no external chemical redox reagents, excellent atom economy, and gram-scale synthesis. In addition, a mechanistic investigation indicates that the reactions proceed through a radical pathway.
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