19980-24-6Relevant articles and documents
2,4,6-TRI-t-BUTYLPHENYLLITHIUM AS A BASE-----KINETIC DEPROTONATION OF BENZYL METHYL KETONE
Yoshifuji, Masaaki,Nakamura, Tetsuo,Inamoto, Naoki
, p. 6325 - 6328 (1987)
An extremely bulky lithium reagent, 2,4,6-tri-t-butylphenyllithium, was applied for deprotonation of benzyl methyl ketone to give the kinetic enol ether by "in situ" quenching with chlorotrimethylsilane as the major product indicating that the reagent serves as a hindered base.
Highly stereoselective oxazaborolidinium ion catalyzed synthesis of (Z)-silyl enol ethers from alkyl aryl ketones and trimethylsilyldiazomethane
Kang, Byung Chul,Shim, Su Yong,Ryu, Do Hyun
, p. 2077 - 2079 (2014/05/06)
Highly stereoselective (Z)-silyl enol ethers were prepared from alkyl aryl ketones and trimethylsilyldiazomethane (TMSD) using an oxazaborolidinium ion catalyst. In addition, ring-expanded silyl enol ethers were successfully constructed from cyclic ketones. Their synthetic utilities were shown by sequential Mukaiyama aldol and [2 + 2]-cycloaddition reactions.
A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimenthylsily)diazomethane in a regiospecific and highly stereoselective manner
Aggarwal, Varinder K.,Sheldon, Chris G.,Macdonald, Gregor J.,Martin, William P.
, p. 10300 - 10301 (2007/10/03)
The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates. Copyright