Efficient one-pot selective reduction of esters in β-ketoesters using LiHMDS and lithium aluminium hydride

K Sivagurunathan, SRM Kamil, SS Shafi, FLA Khan…

Index: Sivagurunathan; Raja Mohamed Kamil; Syed Shafi; Liakth Ali Khan; Ragavan, R. Venkat Tetrahedron Letters, 2011 , vol. 52, # 11 p. 1205 - 1207

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Citation Number: 5

Abstract

As part of our research program, 5 in the synthesis of pyrazoles from β-keto esters, we were interested in the reactivity of enolates of β-keto esters with hydrazines. In this process we were interested in checking the stability and reactivity of ketone enolates. The aryl ketone enolates 2 in aryl β-keto esters were stabilized by their extended conjugation with aromatic systems (Fig. 1) which reduces the reactivity of the ketone to a great extent. These enolized aryl ketones 2 were ...