52657-85-9Relevant academic research and scientific papers
N-heterocyclic carbene-catalyzed conjugate additions of alcohols
Phillips, Eric M.,Riedrich, Matthias,Scheidt, Karl A.
supporting information; experimental part, p. 13179 - 13181 (2010/11/05)
An efficient intermolecular conjugate addition of alcohols to activated alkenes catalyzed by N-heterocyclic carbenes has been developed. With 5 mol % of the free carbene derived from IMes?HCl, unsaturated ketones and esters are competent substrates, and a variety of primary and secondary alcohols can be employed as the nucleophile. No oligomerization is observed under these mild conditions for effective hydroalkoxylation. In addition to reactions with activated alkenes, IMes catalyzes the formation of vinyl ethers through the 1,4-addition of alcohols to ynones and promotes tandem conjugate addition/Michael cascade reactions. Preliminary data support a Bronsted base mechanism with the free carbene.
The efficient synthesis of alkoxy-esters from hydroxy carboxylic acids using dimsyllithium in dimethylsulfoxide followed by alkylation with an alkyl halide
Page, Philip C. Bulman,Chan, Yohan,Heaney, Harry,McGrath, Matthew J.,Moreno, Eduardo
, p. 2606 - 2608 (2007/10/03)
Hydroxy acids are converted directly into the related alkyl ether-alkyl esters in high yields in a single operation by double deprotonation using dimsyllithium in dimethylsulfoxide followed by treatment with an alkyl halide.
