Catalytic enantioselective synthesis of 2-pyrazolines via one-pot condensation/6π-electrocyclization: 3,5-bis(pentafluorosulfanyl)-phenylthioureas as powerful hydrogen bond donors

Abstract

A new conjugate-base-stabilized carboxylic acid (CBSCA) containing a 3,5-bis(pentafluorosulfanyl)phenylthiourea functionality catalyses challenging one-pot condensations/6π-electrocyclizations of hydrazines and α,β-unsaturated ketones under mild conditions. Structurally diverse N-aryl 2-pyrazolines are obtained in good yields and enantioselectivities. The superior performance of 3,5-bis(SF₅)phenylthioureas over the widely used 3,5-bis(CF₃)phenylthioureas is further demonstrated in the Michael addition of dimethyl malonate to nitrostyrene, using a new Takemoto-type catalyst.