Herein, we report a photochemical organocatalytic method for the asymmetric introduction of perfluoroalkyl fragments (including the valuable trifluoromethyl moiety) at the remote gamma-position of alpha-branched enals. The chemistry exploits the ability of extended enamines (dienamines) to form photoactive electron donor-acceptor (EDA) complexes with perfluoroalkyl iodides, which under blue light irradiation generate radicals through an electron transfer mechanism. The use of a chiral organocatalyst, derived from cis-4-hydroxy-l-proline, secures a consistently high stereocontrol while inferring complete site selectivity for the more distal gamma position of the dienamines.
Balletti, M., Wachsmuth, T., Di Sabato, A., Hartley, W.C., Melchiorre, P. (2023). Enantioselective catalytic remote perfluoroalkylation of α-branched enals driven by light. CHEMICAL SCIENCE, 14, 4923-4927 [10.1039/d3sc01347b].
Enantioselective catalytic remote perfluoroalkylation of α-branched enals driven by light
Melchiorre, Paolo
Ultimo
Conceptualization
2023
Abstract
Herein, we report a photochemical organocatalytic method for the asymmetric introduction of perfluoroalkyl fragments (including the valuable trifluoromethyl moiety) at the remote gamma-position of alpha-branched enals. The chemistry exploits the ability of extended enamines (dienamines) to form photoactive electron donor-acceptor (EDA) complexes with perfluoroalkyl iodides, which under blue light irradiation generate radicals through an electron transfer mechanism. The use of a chiral organocatalyst, derived from cis-4-hydroxy-l-proline, secures a consistently high stereocontrol while inferring complete site selectivity for the more distal gamma position of the dienamines.File | Dimensione | Formato | |
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