Brook/Elimination/Aldol Reaction Sequence for the Direct One‐Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes. Issue 4 (9th February 2016)

• Record Type: Journal Article
• Authors: Decostanzi, Mélanie; Godemert, Jérémy; Oudeyer, Sylvain; Levacher, Vincent; Campagne, Jean‐Marc; Leclerc, Eric
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 4(2016)
• Page Start: 526
• Page End: 531
• Publication Date: 2016-02-09
• Subjects: aldol reaction -- Brook rearrangement -- fluorine -- organocatalysis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500849
• Languages: English
• ISSNs: 1615-4150

Abstract

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. Abstract :