Synthesis 2017; 49(17): 4082-4092
DOI: 10.1055/s-0036-1588447
paper
© Georg Thieme Verlag Stuttgart · New York

A Three-Component Reaction for the One-Pot Preparation of β-Amino-α,α-Difluoroketones from Trimethyl(trifluoromethyl)silane (CF3TMS), Acylsilanes and Imines

Aurélien Honraedt
Institut Charles Gerhardt UMR 5253 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France   Email: [email protected]
,
Lucía Reyes Méndez
Institut Charles Gerhardt UMR 5253 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France   Email: [email protected]
,
Jean-Marc Campagne
Institut Charles Gerhardt UMR 5253 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France   Email: [email protected]
,
Eric Leclerc*
Institut Charles Gerhardt UMR 5253 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 11 April 2017

Accepted after revision: 05 May 2017

Publication Date:
13 June 2017 (online)


Abstract

A methodology allowing the direct preparation of β-amino-α,α-difluoroketones from the Ruppert–Prakash reagent (CF3TMS), acyltrimethylsilanes and N-Boc or N-(diphenylphosphinyl)imines is reported. The process, initiated by a catalytic amount of tetra-n-butylammonium difluorotriphenylsilicate (TBAT), involves the addition of CF3TMS to the acylsilane, followed by a Brook rearrangement and elimination of a fluoride anion. The latter promotes the addition of the resulting difluoroenoxysilane to the imine. The higher electrophilicity of the acylsilane compared to the imine allows the direct mixing of all the reagents in a three-component, one-pot process.

Supporting Information

 
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