C 2 -symmetric sulfonamides as homogeneous and heterogeneous organocatalysts that mimic enzymes in enantioselective Michael additions

Herein, we report the synthesis of C -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...

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Bibliographic Details
Published inChirality (New York, N.Y.) Vol. 30; no. 8; pp. 1036 - 1044
Main Authors Cruz, Harold, Servín, Felipe A, Madrigal, Domingo, Chávez, Daniel, Perez-Sicairos, Sergio, Aguirre, Gerardo, Cooksy, Andrew L, Somanathan, Ratnasamy
Format Journal Article
LanguageEnglish
Published United States 01.08.2018
Subjects
density functional calculations
β-nitrostyrene
transition state
immobilized organocatalyst
conjugate addition
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Summary:Herein, we report the synthesis of C -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.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22984