Brook/Elimination/Aldol Reaction Sequence for the Direct One-Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes - Normandie Université Access content directly
Journal Articles Advanced Synthesis and Catalysis Year : 2016

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.

Dates and versions

hal-02046202 , version 1 (22-02-2019)

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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, 2016, 358 (4), pp.526-531. ⟨10.1002/adsc.201500849⟩. ⟨hal-02046202⟩
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