444168-97-2Relevant academic research and scientific papers
Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function
Ding, Pingyu,Ghosez, Léon
, p. 1565 - 1571 (2007/10/03)
1,1-Dimethyl-3-(phenylthio)-propane 4 was deprotonated with t-BuLi, then converted to the corresponding organocuprate reagent which, in the presence of HMPA and TMSCI, was added to a variety of enones to give the corresponding silylenol ethers 7. These were cyclised without purification upon acidic conditions to give the cyclopentannulation products 9. A similar result was obtained with the corresponding orthoester reagent 6. This cyclopentannulation sequence is applicable to a wide variety of enones except for those bearing substituents near the reacting centre.
