Aliphatic Nitro Compounds as Pronucleophiles

Aliphatic nitro compounds are intermediates with considerable potential in orgarhc synthesis (cf. Section 9.6). Irhhally, ahyhc substitutions with nitromethane were investigated, but unfortunately complex mixtures of mono- and dialkylation products were formed. In contrast, good results were obtained with primary and 

Commercially available ethyl nitroacetate is an interesting pronucleophile, because it can serve as the synthetic equivalent of either nitromethane or glycine. The ethoxycarbonyl group can also be considered as a protecting group against dialkylation. The allylic alkylation with ethyl nitroacetate did not require an additional base (salt-free conditions). As a consequence of the high acidity of the chirality center a to N, 1 1 mixtures of epimers were formed. 

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