AgOAc Catalyzed Asymmetric [3+2] Cycloaddition Of Azomethine Ylides With Chiral Ferrocene Derived Phosphine-amine Ligand

Asymmetric [3+2] cycloadditon reactions of azomethine ylides with AgOAc and phosphine-amine ligands derived from chiral ferrocene have been studied. Then, 1-substituted isoquinolines were concisely synthesized by the reactions of 1-substituted-N-Cbz-1,2-dihydroisoquinolines being deprotected and aromatized under the condition of Pd/C/HCO2NH4.1. AgOAc Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides with Chiral Ferrocene Derived Phosphine-amine Ligands.The [3+2] cycloaddition reactions of azomethine ylides with electronic-deficient alkenes provided a convenient route to synthesize optically active pyrrolidine derivatives. A series of chiral ferrocene derived phosphine-amine ligands were easily synthesized from commercial available starting materirals. We found that ferrocene derived chiral phosphine-amine ligand can be applied to bifunctional AgOAc catalyzed [3+2] reactions with high reactivity and excellent enantioselectivity. It is noteworthy that reverse asymmetric induction can be obtained by using the phosphine-NH2 and phosphine-NMe₂ ligands with the same chiral motif.