Catalytic Tandem Conjugate Addition-Electrophilic Fluorination For The Synthesis Of Chiral Fluorine-containing Compounds

Tandem reaction has attracted considerable attention in recent years. It enables a rapid increase in molecular complexity and diversity from readily available starting compounds and forms several covalent bonds in one-pot, it is an efficient synthesis strategy of constructing complicated organic compounds economically and conveniently.In conjugate addition reactions of organozinc reagents, monodentate phosphoramidite ligands were found to be more efficient. In this work, high enantioselectivities were achieved in copper-catalyzed asymmetric tandem conjugate addition-electrophilic fluorination reactions by using chiral BINOL-derived phosphoramidite ligands.3, 3'-Disubstituted BINOL-derived phosphoramidite ligands were prepared from optically pure BINOL. By changing the substitutes at 3, 3'-position and amine moieties, fourteen chiral phosphoramidite ligands were obtained.By using 3, 3'-Disubstituted BINOL-derived phosphoramidite ligands, copper-catalyzed asymmetric tandem conjugate addition-electrophilic fluorination reactions afforded the corresponding chiral fluorine-containing compounds in high yield with high diastero- (up to 93/7) and enantioselectivities (up to 76%ee). The reaction provided a useful method for preparing chiral fluorine-containing compounds.