biostudies-literatureUnknown20Bilska-Markowska MThe incorporation of fluorine atoms within the structure of organic compounds is known to exert a significant impact on their electronic properties, thereby modulating their reactivity in diverse chemical transformations. In the context of our investigation, we observed a striking illustration of this phenomenon. A Michael addition involving <i>gem</i>-difluorovinyl and trifluorovinyl acceptors was successfully achieved, demonstrating high stereoselectivity. This selectivity was further elucidated through theoretical calculations. Using this methodology, a series of new α,β-unsaturated amides, both fluorinated and nonfluorinated, were synthesized.Beilstein journal of organic chemistry2946-2953https://www.ebi.ac.uk/biostudies/studies/S-EPMC11572014biostudies-literature&lt;i&gt;gem&lt;/i&gt;-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides.PMC11572014Kazmierczak MHoffmann MJankowski WBilska-Markowska Mfalse&lt;i&gt;gem&lt;/i&gt;-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides.The incorporation of fluorine atoms within the structure of organic compounds is known to exert a significant impact on their electronic properties, thereby modulating their reactivity in diverse chemical transformations. In the context of our investigation, we observed a striking illustration of this phenomenon. A Michael addition involving <i>gem</i>-difluorovinyl and trifluorovinyl acceptors was successfully achieved, demonstrating high stereoselectivity. This selectivity was further elucidated through theoretical calculations. Using this methodology, a series of new α,β-unsaturated amides, both fluorinated and nonfluorinated, were synthesized.2024-01-01T00:00:00Z20242025-04-04T02:51:06.444Z2025-04-04T02:51:06.444ZS-EPMC115720143955944210.3762/bjoc.20.247