80522-46-9Relevant articles and documents
One-Pot Synthesis of Silylated Enol Triflates from Silyl Enol Ethers for Cyclohexynes and 1,2-Cyclohexadienes
Inoue, Kazuki,Nakura, Ryo,Okano, Kentaro,Mori, Atsunori
supporting information, p. 3343 - 3347 (2018/07/13)
Regiocontrolled synthesis of precursors for strained cyclohexynes and 1,2-cyclohexadienes is described based on one-pot rearrangement of silyl enol ether followed by formation of enol triflate. Treatment of silyl enol ether with a combination of LDA and tBuOK led to the migration of the silyl group to generate α-silyl enolate, which was treated with Comins' reagent to provide the corresponding enol triflate. The transient α-silylated lithium enolate was smoothly isomerized in the presence of stoichiometric amount of water within one hour at room temperature, providing precursors for cyclohexynes exclusively in one pot. Effects of silyl groups, isomerization of the lithium enolate, and regiocontrolled generation of these precursors for these strained molecules were also investigated.
Catalytic [3+2] annulation of aminocyclopropanes for the enantiospecific synthesis of cyclopentylamines
De Nanteuil, Florian,Waser, Jerome
supporting information; experimental part, p. 12075 - 12079 (2012/02/14)
With nitrogen too: The first catalytic [3+2] annulation of aminocyclopropanes with enol ethers is reported (see scheme; Phth=phthaloyl). The reaction worked with easily accessible phthalimidocyclopropanes using 5 mol % of SnCl4 in nearly quantitative yields. Polysubstituted cyclopentylamines, which are often present in bioactive compounds, were obtained with high diastereoselectivity and enantiospecificity. Copyright
Pd(OH)2/C-mediated selective oxidation of silyl enol ethers by tert-butylhydroperoxide, a useful method for the conversion of ketones to α,β-enones or β-Silyloxy-α,β-enones
Yu, Jin-Quan,Wu, Hai-Chen,Corey
, p. 1415 - 1417 (2007/10/03)
(Chemical Equation Presented) Pd(OH)2-catalyzed oxidation of silyl enol ethers by t-BuOOH gives either β-silyloxy-α,β-enones or α,β-enones in good yields depending on the base used.