Pd-Catalyzed Asymmetric Addition of Arylboronic Acids to Pyrazolinone Ketimines

An-Qi Miao, Meng Zhou, Jing-Long Chen, Shi-Chao Wang, Wen-Juan Hao,* Shu-Jiang Tu,* Bo Jiang*

An asymmetric addition of arylboronic acids to pyrazolinone ketimines is reported using palladium/chiral N,N′-disulfonyl bisimidazoline (Bim) catalytic system, producing 25 examples of enantioenriched 4-amino-5-pyrazolones bearing one quaternary carbon stereocenter with 60-91% yields and 81-98% ee. The reaction demonstrates remarkable compatibility regarding pyrazolinone ketimines and arylboronic acids, rendering an enantioselective access to chiral aza-heterocycles bearing α-tertiary amines

Adv. Synth. Catal. 2021, 363, 5162-5166; DOI: 10.1002/adsc.202101137