Ir-Catalyzed Asymmetric Allylic Substitution of Hydrazine Derivatives

For the synthesis of chiral hydrazine-containing intermediate 2a, enantioselective allylic substitution using N-aminophthalimide was evaluated. A method was developed that enabled the desired transformation to be performed in an enantioselective and regioselective manner. The substrate scope with respect to hydrazine derivatives and different allylic carbonates was evaluated. A telescoped sequence for phthalimide deprotection and pyrazole synthesis without the need to isolate the deprotected hydrazine intermediate was also demonstrated.