Organocatalyzed one‐pot sequential deracemization of aromatic ketones bearing a tertiary stereogenic center
Abstract
An organocatalyzed one-pot sequential deracemization of aromatic ketones bearing a stereogenic center at the a-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 having 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.
Domains
Organic chemistry
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