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- Title
Chiral C<sub>2</sub>‐symmetric bis‐thioureas as enzyme mimics in enantioselective Michael addition.
- Authors
Cruz, Harold; Servín, Felipe A.; Aguirre, Gerardo; Pérez, Sergio; Madrigal, Domingo; Chávez, Daniel; Cooksy, Andrew L.; Somanathan, Ratnasamy
- Abstract
We report herein the synthesis and application of enantiopure C2‐symmetric primary amine‐1,3‐bis‐thiourea organocatalysts in enantioselective conjugate 1,4‐Michael addition of carbonyl containing nucleophiles, to nitroalkenes and N‐phenylmaleimide, leading to final products in good enantioselectivities (up to 99%) and yields (up to 99%). We propose supramolecular noncovalent interactions within the organocatalyst's cleft between the substrate and the catalyst, via hydrogen bonding. Supramolecular interaction thus lowers the transition state energy mimicking an enzyme. Mechanism underlying our experimental results is supported by theorical calculations.
- Subjects
THIOUREA; ENZYMES; HYDROGEN bonding; ENERGY policy; NITROALKENES; NUCLEOPHILES; CARBONYL compounds
- Publication
Chirality, 2022, Vol 34, Issue 6, p877
- ISSN
0899-0042
- Publication type
Article
- DOI
10.1002/chir.23438