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C 2 ‐symmetric sulfonamides as homogeneous and heterogeneous organocatalysts that mimic enzymes in enantioselective Michael additions
Author(s) -
Cruz Harold,
Servín Felipe A.,
Madrigal Domingo,
Chávez Daniel,
PerezSicairos Sergio,
Aguirre Gerardo,
Cooksy Andrew L.,
Somanathan Ratnasamy
Publication year - 2018
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22984
Subject(s) - chemistry , enantioselective synthesis , michael reaction , enamine , nucleophile , conjugate , organocatalysis , homogeneous , catalysis , hydrogen bond , organic chemistry , combinatorial chemistry , molecule , mathematics , mathematical analysis , physics , thermodynamics
Abstract Herein, we report the synthesis of C 2 ‐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.