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- Title
C<sub>2</sub>‐symmetric sulfonamides as homogeneous and heterogeneous organocatalysts that mimic enzymes in enantioselective Michael additions.
- Authors
Cruz, Harold; Servín, Felipe A.; Madrigal, Domingo; Chávez, Daniel; Perez‐Sicairos, Sergio; Aguirre, Gerardo; Cooksy, Andrew L.; Somanathan, Ratnasamy
- Abstract
Abstract: Herein, we report the synthesis of C2‐symmetric sulfonamides as homogeneous and heterogeneous organocatalysts and their application in the enantioselective conjugate 1,4‐Michael addition of carbonylic nucleophiles to β‐nitrostyrene. Organocatalysts hydrogen bond to β‐nitrostyrene and enamine in the transition state, mimicking an enzyme leading to final products in high yields (up to 98%) and good enantioselectivities (up to 96%). In addition, these results were supported by density functional calculations.
- Subjects
SULFONAMIDES; ORGANOCATALYSIS; ENANTIOSELECTIVE catalysis; MICHAEL reaction; NUCLEOPHILES
- Publication
Chirality, 2018, Vol 30, Issue 8, p1036
- ISSN
0899-0042
- Publication type
Article
- DOI
10.1002/chir.22984