Organocatalyzed One‐Pot Sequential Deracemization of Aromatic Ketones Bearing a Tertiary Stereogenic Center

Abstract

AbstractAn organocatalyzed one‐pot sequential deracemization of aromatic ketones bearing a stereogenic center at the α‐position was achieved thanks to an acid‐base strategy involving an enantioselective protonation reaction as a key step. This simple and efficient protocol yields enantioenriched ketones in up to 89% ee without the need to isolate sensitive intermediates such as silyl enolates. The key role of water in this process was underlined. This one‐pot sequence constitutes a useful extension to previously reported chemically driven red‐ox protocols, thus increasing the panel of molecules eligible to a deracemization strategy.magnified image