Chiral-Boron-Complex-Catalyzed Asymmetric [3 + 2] Cycloaddition of 2'-Hydroxychalcones with N,N'-Cyclic Azomethine
Guo-Li Chai1, En-Ze Yao1, Rui-Hao Liu1
1NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China.
Abstract:
We report the (R)-3,3'-I2-BINOL-boron-complex-catalyzed asymmetric 1,3-dipolar cycloaddition of 2'-hydroxychalcones with N,N'-cyclic azomethine imines, providing the corresponding N,N'-bicyclic pyrazolidine derivatives with three contiguous tertiary stereocenters in high yields with excellent diastereo- and enantioselectivities (up to >99:1 diastereomeric ratio and >99% enantiomeric excess). This catalytic system exhibits advantages of mild reaction conditions, high efficiency, and broad substrate scopes.
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