85429-35-2Relevant academic research and scientific papers
Enamines β-lithiees. I. Preparations et reactions d'alkylation
Duhamel, Lucette,Poirier, Jean-Marie
, p. 297 - 303 (2007/10/02)
The action of alkyllithium reagents on β-bromoenamines 1-9 quickly yields, in THF, β-lithioenamines through halogen - metal exchange.If metallic lithium is used instead of organolithium compounds, β-lithioenamines are also formed but in this case they are accompanied by small amounts of by-products.The action of alkyllithium reagents R1Li on the β-chloroenamine 10 provides a new source of β-lithioenamines in which nucleophilic insertion of the R1 group takes place. β-Lithioenamines are stable compounds even up to 20 deg C in most cases.With alkyl iodides, β-lithioenamines react vigorously even at low temperature.The reaction is stereospecific with retention of configuration.This reaction generates either β-substituted enamines or, by easy acidic hydrolysis, α-substituted carbonyl compounds.The C-alkylation reaction is observed alone.
