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

Wei-Tai Fan¹, Xiao-Peng Yang¹, Hao-Peng Lv¹, Xing-Wang Wang^1*（王兴旺）, and Zheng Wang^2*（王正）

¹Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, the People’s Republic of China

²State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Shanghai 200032, the People’s Republic of China

Org. Lett. 2020, 22, 3936--3941

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.

链接：https://pubs.acs.org/doi/abs/10.1021/acs.orglett.0c01221