Reaction of O-benzyl-N-methylenehydroxylamine with organolithium compounds, a CH₂⁺–NH⁺synthetic equivalent

Electrophilic Amination: The Case of Nitrenoids

“…Basha and Brooks employed an alternative method to generate lithium nitrenoids 19 from oxime 18 and explored their applicability to aminate a second organolithium reagent (Scheme ) 25. Despite the fact that addition of a first organolithium across the oxime 18 occurred rapidly at −40 °C, the amination stage required warming up to 0 °C and even 40 °C for 1–3 h.…”

“…Basha and Brooks envisaged the addition of alkyl and aryllithium compounds across oxime 18 to give the desired lithium nitrenoid 19 (Scheme ; for particular examples using this route, see Section 3.2) 25…”

Nucleophilic Addition to Imines and Imine Derivatives

“…alkyllithium reagent (primary, secondary and tertiary carbanions) provides, after axial protonation, 3~-alkylcholestane products (116) in addition to minor amounts of the anticipated alkene by-products (equation 16).99…”

Chemoselective addition of organometallics to oxime ethers

“…These three component reactions are interesting and important, not only because of forming two bonds in one reaction, but also because this methodology would be useful for making a broad variety of nitrogen-containing compounds [8,9]. Although the original mannich reaction was carried out with amines, these reactions can be performed with other N-heterosubstituted amines such as hydrazones and oximes [10][11][12][13][14].…”