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  • Title: Enantioselective catalytic remote perfluoroalkylation of α-branched enals driven by light.
    Author: Balletti M, Wachsmuth T, Di Sabato A, Hartley WC, Melchiorre P.
    Journal: Chem Sci; 2023 May 10; 14(18):4923-4927. PubMed ID: 37181764.
    Abstract:
    Herein, we report a photochemical organocatalytic method for the asymmetric introduction of perfluoroalkyl fragments (including the valuable trifluoromethyl moiety) at the remote γ-position of α-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 γ position of the dienamines.
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