Abstract
alpha-Triisopropylsilyl-alpha-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 16 degrees C, in Et(2)0. Robustness of the TIPS group makes TIPS-diazoacetone a stable surrogate for alpha-triethylsilyl-alpha-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. (C) 2016 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.