Tetrahedron letters

Metalation of α-diazocarbonyl compounds using Grignard reagents. A convenient synthesis of α-diazo-β-ketoesters and mixed esters of α-diazomalonate

E Cuevas-Yañez, JM Muchowski, R Cruz-Almanza

Index: Cuevas-Yanez, Erick; Muchowski, Joseph M.; Cruz-Almanza, Raymundo Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2417 - 2419

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Citation Number: 8

Abstract

α-Diazocarbonyl compounds react with methylmagnesium bromide at− 78° C generating the corresponding α-diazo-α-bromomagnesio species, which can be intercepted by various electrophilic reagents. For example, with alkyl chloroformates α-diazo-β-ketoesters or mixed esters of α-diazomalonate are obtained in good yields.