Construction of central and axial chirality via Pd(II)/Bim-catalyzed asymmetric dearomative Michael reaction of polycyclic tropones

Zi-Li Liu, Yu-Xin Wang, Zi-Qi Yang, Yu-Heng Yang, Yin-Ping Liu, Wen-Juan Hao,* Bo Jiang*

A highly enantioselective Pd/Bim-catalyzed dearomative Michael reaction applying polycyclic tropones as a non-benzenoid aromatic Michael acceptor and arylboronic acids as aryl pronucleophiles has been developed. The bridged biaryls bearing central and axial chirality, including pentacyclic cyclohepta[b]indoles and 6,7-dihydrodibenzo[a,c][7]annulen-5-ones, are generally generated in good to high yields and excellent enantioselectivities and can be readily transformed into useful derivatives.

Chem. Commun. 2024, 60, 8908-8911; DOI:10.1039/D4CC03166K