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Chiral Binaphthyl Box-Copper-Catalyzed Enantioselective Tandem Michael–Ketalization Annulations for Optically Active Aryl and Heteroaryl Fused Bicyclicnonanes

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journal contribution
posted on 01.05.2020, 16:36 by Wei-Tai Fan, Xiao-Peng Yang, Hao-Peng Lv, Xing-Wang Wang, Zheng Wang
The combination of chiral binaphthyl box-copper­(II) with triflimide (Tf2NH) was identified as an efficient catalytic system for the asymmetric Michael/ketalization of (E)-2-hydroxyaryl-2-oxobut-3-enoates or (E)-ethyl 4-(2-aminoaryl)-2-oxobut-3-enoates with pyrazolone derivatives. The corresponding asymmetric tandem reactions provided a series of enantioenriched aryl and heteroaryl fused 2,8-O,O- or O,N-bicyclo­[3.3.1]­nonanes in high yields with excellent enantio- and diastereoselectivities.