Fig. 6: Gram-scale reaction and synthetic application.

a Gram-scale reaction. b Transformation of the benzyl-protected tetrahydroquinoline. c Synthesis of potential selective estrogen receptor modulator (SERMs) 23. Ac, acetyl; Ar, aryl; Bn, benzyl; Me, methyl; Et, ethyl; Ph, phenyl; (Bpin)2, bis(pinacolato)diboron; DMF, N,N-dimethylformamide; DME, 1,2-dimethoxyethane; DCM, dichloromethane; [BMIM]BF4, 1-butyl-3-methylimidazolium tetrafluoroborate; dppb, 1,4-bis(diphenylphosphino)butane; MePhos, 2-(dicyclohexylphosphino)−2’-methylbiphenyl.