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Organocatalytic Aza-Friedel–Crafts/Lactonization Domino Reaction of Naphthols and Phenols with 2‑Acetamidoacrylate to Naphtho- and Benzofuranones Bearing a Quaternary Center at the C3 Position

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journal contribution
posted on 07.09.2018, 00:00 by Francesca Bartoccini, Michele Mari, Michele Retini, Silvia Bartolucci, Giovanni Piersanti
N-Acetyl ketimine generated from methyl 2-acetamidoacrylate was explored to develop an unprecedented domino aza-Friedel–Crafts/lactonization reaction with naphthols and phenols (including 5-hydroxyindoles). This novel method requires a catalyst loading of only 5 mol % of a phosphoric acid catalyst and provides a new series of 3-NHAc-naphtho- and benzofuranone derivatives bearing tetra-substituted stereogenic centers in moderate-to-good yields. The enantioselective variant using BINOL-derived phosphoric acids was also explored with 1-naphthol, providing the desired product with moderate enantioselectivities (up to 99:1 following recrystallization).