“On Water” Nucleophilic Addition of Formaldehyde N,N-Dialkylhydrazoneto a-Keto Esters

4 paginas, 4 esquemas, 2 tablasWater 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.We thank the Spanish Ministerio de Ciencia e Innovaci n (grant numbers CTQ2010-15297 and CTQ2010-14974), the European FEDER funds, and the Junta de Andaluc a (grant numbers 2008/FQM-3833 and 2009/FQM4537) for financial support. A.C. thanks the Agencia Consejo Superior de Investigaciones Cient ficas for a JAE predoctoral fellowship.Peer reviewe

“On Water” Nucleophilic Addition of Formaldehyde N,N-Dialkylhydrazoneto a-Keto Esters

4 paginas, 4 esquemas, 2 tablasWater 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.We thank the Spanish Ministerio de Ciencia e Innovaci n (grant numbers CTQ2010-15297 and CTQ2010-14974), the European FEDER funds, and the Junta de Andaluc a (grant numbers 2008/FQM-3833 and 2009/FQM4537) for financial support. A.C. thanks the Agencia Consejo Superior de Investigaciones Cient ficas for a JAE predoctoral fellowship.Peer reviewe