197958-57-9Relevant academic research and scientific papers
Generation of allylic and benzylic organolithium reagents from the corresponding ester, amide, carbonate, carbamate and urea derivatives
Alonso, Emma,Guijarro, David,Martinez, Pedro,Ramon, Diego J.,Yus, Miguel
, p. 11027 - 11038 (2007/10/03)
The reaction of different allylic and benzylic non-enolisable esters or amides (1), carbonates (4), carbamates (6, 7) and ureas (8) with an excess of lithium powder and a catalytic amount of naphthalene (10%) in the presence of an electrophile [(i)PrCHO, (t)BuCHO, PhCHO, Me2CO, Et2CO, (CH2)5CO, Ph2CO, Me3SiCl] in THF at different temperatures (-78, -30 or 0°C) leads, after hydrolysis with water to the corresponding allylated or benzylated products (2).
Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
, p. 14355 - 14368 (2007/10/03)
The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene (4 mol %) in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective.
