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Brook/Elimination/Aldol Reaction Sequence for the Direct One‐Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes
Author(s) -
Decostanzi Mélanie,
Godemert Jérémy,
Oudeyer Sylvain,
Levacher Vincent,
Campagne JeanMarc,
Leclerc Eric
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500849
Subject(s) - trimethylsilane , chemistry , aldol reaction , reagent , trifluoromethyl , fluoride , catalysis , aldol condensation , trifluoromethylation , salt (chemistry) , ammonium , organic chemistry , inorganic chemistry , alkyl
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.