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Brook/Elimination/Aldol Reaction Sequence for the Direct One-Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes

Abstract : A methodology allowing the one‐pot preparation of difluorinated aldols directly from Ruppert–Prakash reagent, acyltrimethylsilanes and aldehydes is reported. The process, initiated by a catalytic amount of an ammonium salt, involves the addition of (trifluoromethyl)trimethylsilane to the acylsilane, followed by a Brook rearrangement and elimination of a fluoride anion that promotes the subsequent aldol reaction. An efficient racemic reaction catalyzed by tetrabutylammonium difluorotriphenylsilicate is described, as well as our first efforts towards an asymmetric version.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046202
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:36:32 PM
Last modification on : Thursday, July 2, 2020 - 3:28:45 AM

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Mélanie Decostanzi, Jérémy Godemert, Sylvain Oudeyer, Vincent Levacher, Jean-Marc Campagne, et al.. Brook/Elimination/Aldol Reaction Sequence for the Direct One-Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2016, 358 (4), pp.526-531. ⟨10.1002/adsc.201500849⟩. ⟨hal-02046202⟩

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