C2‐symmetric sulfonamides as homogeneous and heterogeneous organocatalysts that mimic enzymes in enantioselective Michael additions |
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| Authors: | Harold Cruz Felipe A Servín Domingo Madrigal Daniel Chávez Sergio Perez‐Sicairos Gerardo Aguirre Andrew L Cooksy Ratnasamy Somanathan |
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| Institution: | 1. Centro de Graduados e Investigación en Química del Instituto Tecnológico de Tijuana, Tijuana, B.C., Mexico;2. Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA, USA |
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| 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. |
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| Keywords: | conjugate addition density functional calculations immobilized organocatalyst transition state β ‐nitrostyrene |
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