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.
Article
in En
| MEDLINE
| ID: mdl-39239480
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,ß-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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Chem Sci
Year:
2024
Document type:
Article
Country of publication:
United kingdom