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Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2022

Organocatalyzed one‐pot sequential deracemization of aromatic ketones bearing a tertiary stereogenic center

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-03822325 , version 1 (20-10-2022)

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Claire Segovia, Jérémy Godemert, Jean-François Brière, Vincent Levacher, Sylvain Oudeyer. Organocatalyzed one‐pot sequential deracemization of aromatic ketones bearing a tertiary stereogenic center. Advanced Synthesis and Catalysis, 2022, 364 (22), pp.3794-3799. ⟨10.1002/adsc.202200857⟩. ⟨hal-03822325⟩
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