53282-55-6Relevant articles and documents
Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark
Anderson,Andia, Alexander A.,Woerpel
supporting information, (2021/02/03)
The hydroperoxidation of alkyl enol ethers using N-hydroxyphthalimide and molecular oxygen occurred in the absence of catalyst, initiator, or light. The reaction proceeds through a radical mechanism that is initiated by N-hydroxyphthalimide-promoted autoxidation of the enol ether substrate. The resulting dioxetane products decompose in a chemiluminescent reaction that allows for photochemical activation of N-hydroxyphthalimide in the absence of other light sources.
Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3-Metalate Rearrangement of Lithium Enolates
Hu, Yue,Sun, Wei,Zhang, Tao,Xu, Nuo,Xu, Jianeng,Lan, Yu,Liu, Chao
supporting information, p. 15813 - 15818 (2019/10/28)
An unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C?O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled by sterics. A variety of stereospecific trisubstituted vinylboronates, together with several tetrasubstituted vinylboronates, were conveniently synthesized with the newly developed methodology. Based on the transformation of stereospecific vinylboronate, a single isomer of Dienestrol was efficiently obtained.
Preparation of silyl enol ethers using (bistrimethylsilyl)acetamide in ionic liquids
Smietana, Michael,Mioskowski, Charles
, p. 1037 - 1039 (2007/10/03)
(matrix presented) Ionic liquids have been used for the preparation of silyl enol ethers from aldehydes and ketones with (bistrimethylsilyl)acetamide (BSA) in good yields.