106435-59-0Relevant articles and documents
Advances in the TBAF-induced aldol-type addition of α-trialkylsilyl-α-diazoacetones: TIPS versus TES
Abid, Imen,Gavelle, Sigrid,Chany, Anne-Caroline,Legros, Frédéric,Gosselin, Pascal,Abid, Souhir,Dujardin, Gilles,Gaulon-Nourry, Catherine
, p. 595 - 600 (2017)
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 ?16 °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.
Thermal Decomposition of α-Diazo-α-(trialkylsilyl)alkanones - Intramolecular C/H Insertion of Siloxyalkylidenecarbene Intermediates
Brueckmann, Ralf,Maas, Gerhard
, p. 635 - 642 (2007/10/02)
α-Diazo-α-(trialkylsilyl)alkanones 6 have been prepared by silylation of primary α-diazo ketones 4 with trialkylsilyl triflates 5.Diazo compounds 6 are decomposed in boiling benzene to give 1-oxa-2-sila-4-cyclopentenes 7 and 9.Evidence is presented that this transformation proceeds via alkylidenecarbenes 17 which undergo 1,5-cyclization by carbene insertion into a SiC-H bond.