![]() A remarkable reactivity difference, however, arises upon silylation of these anions: whereas a silylated enolate exhibits high nucleophilicity and reacts with various classes of electrophiles in Lewis-acid-mediated, Mukaiyama-type reactions, the silylation of a nitronate anion creates a bi-reactive species, a so-called ambiphile, which can react with both electrophiles and nucleophiles 1. Nitroalkanes, like carbonyl compounds, upon deprotonation engage in useful (catalytic) transformations with electrophiles, including Henry- and Michael-type reactions.
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