Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
6468795 | Comptes Rendus Chimie | 2017 | 6 Pages |
Abstract
α-Triisopropylsilyl-α-diazoacetone (TIPS-diazoacetone) underwent high-yielding “diazo-side” Mukaiyama aldol-type addition with a range of aryl and alkyl aldehydes when subjected to stoichiometric amount of tetrabutylammonium fluoride at â16 °C, in Et2O. Robustness of the TIPS group makes TIPS-diazoacetone a stable surrogate for α-triethylsilyl-α-diazoacetone, on which generation of the corresponding carbanion can still be efficiently achieved under nucleophilic, weakly basic and practical conditions. These results highlight the synthetic potential that can be expected from TIPS-diazoacetone, promising building block for the convergent elaboration of highly functionalised versatile diazocarbonyl compounds.
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Authors
Imen Abid, Sigrid Gavelle, Anne-Caroline Chany, Frédéric Legros, Pascal Gosselin, Souhir Abid, Gilles Dujardin, Catherine Gaulon-Nourry,