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"On Water" Nucleophilic Addition of Formaldehyde N,N-Dialkylhydrazones to α-Keto Esters


Ana Crespo-Peña, Eloísa Martín-Zamora, Rosario Fernández y José María Lassaletta Chemistry - An Asian Journal 2012, Vol. 10, 2287–2290

Water solves the problem: The use of pure water as the reaction mixture is key for the nucleophilic addition of formaldehyde hydrazones to α-keto esters, leading to highly functionalized carbinols in high yields and short reaction times. The need for heterogeneous conditions and the observed solvent kinetic isotope effect are in agreement with the proposed “on water” activation.