82588-88-3Relevant articles and documents
Doubly Deprotonated Methyl 3-Nitropropanoate, an Acrylic Ester d2-Reagent
Seebach, Dieter,Henning, Rainer,Mukhopadhyay, Triptikumar
, p. 1705 - 1720 (2007/10/02)
Methyl 3-nitropropanoate can be doubly deprotonated with LDA, both in the α-nitro and in the α-carbonyl position (-> 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-dialkyl-β-nitropropanoate 5 is possible.Elimination of HNO2 with DBN or even better with DBU in THF furnishes methyl α-methylenealkanoates 9 and methyl β-hydroxy-α-methylenealkanoates 10.