Chemische Berichte

Doubly Deprotonated Methyl 3??Mitropropanoate, an Acrylic Ester d2??reagent

…, R Henning, T Mukhopadhyay

Index: Seebach, Dieter; Henning, Rainer; Mukhopadhyay, Triptikumar Chemische Berichte, 1982 , vol. 115, # 5 p. 1705 - 1720

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Citation Number: 66

Abstract

Abstract Methyl 3-nitropropanoate can be doubly deprotonated with LDA, both in the α-nitro and in the α-carbonyl position ([RIGHTWARDS ARROW] 1). It is shown that the necessary cosolvent HMPT can be replaced by the cyclic urea DMPU, with almost equal results. The new reagent 1 is alkylated and hydroxyalkylated by alkyl halides and aldehydes, respectively, at the 2-position exclusively (see 2, 4, 6, 7). A double alkylation to methyl α, α ...