I am looking for addition of nucleophile on double bond of unsaturated carbonyl compound.
It is possible when I am using any catalyst but without catalyst reaction doesn't proceed. There are many catalyst used for Michael addition such as Cinchona based or metal complexes but they will give asymmetric adduct while I am looking for the racemic adduct.
See for inspiration https://www.researchgate.net/publication/269775781_Efficient_solid_support_catalyzed_mono-aza-Michael_addition_reactions_of_piperazine
Article Efficient solid support catalyzed mono-aza-Michael addition ...
The right catalytic system will depend somewhat on the nucleophile you are using.
Cu(I) salts, Morpholine and TMSCl can be good catalysts depending on your exact system.
Hi Eric,
I am using tert-butylhydroperoxide as nucleophile. I am not clear about the reaction you asked me to use having Cu(I)/Morpholine/TMSCl.
Would you provide some ref. ?
So, presumably you want to obtain the epoxide, rather than the isolated Michael adduct?
Tetrabutylammonium hydroxide in THF/H2O should be worth a look, as phase transfer conditions work well in this system. Zn or Mg are good choices for lewis acids.
Hi Eric, I am not actually trying to obtain epoxide rather I am getting Michael adduct.
No matter, the change of solvent done a trick for me. I got 51:49 ratio for R and S respectively.
Thanks for your answers!!!
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