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

Chem Sci. 2024 Aug 26;15(37):15456-15462. doi: 10.1039/d4sc04760e. Online ahead of print.

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.