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

Moises A Romero ReyesSubhradeep DuttaMinami OdagiChang MinDaniel Seidel
Published in: Chemical science (2024)
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(SF 5 )phenylthioureas over the widely used 3,5-bis(CF 3 )phenylthioureas is further demonstrated in the Michael addition of dimethyl malonate to nitrostyrene, using a new Takemoto-type catalyst.
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