152718-41-7Relevant academic research and scientific papers
Lewis acid catalysed [4+2] heterocycloadditions between ketone enol ethers and β-ethylenic α-oxo esters
Martel, Arnaud,Leconte, Stephane,Dujardin, Gilles,Brown, Eric,Maisonneuve, Vincent,Retoux, Richard
, p. 514 - 525 (2002)
The [4+2] heterocycloaddition reaction between (E)-γ-substituted β-unsaturated α-oxo esters 1a-d and cyclic and acyclic ketone enol ethers 2a-l afforded heteroadducts 3-5 in high yields when either [Eu(fod)3] or SnCl4 were used as th
Eu(fod)3 and SnCl4-catalyzed heterocycloadditions of O-silyl enol ethers deriving from cyclic ketones
Dujardin, Gilles,Martel, Arnaud,Brown, Eric
, p. 8647 - 8650 (1998)
O-t-Butyldimethylsilyl enol ethers deriving from simple cyclic ketones acted as efficient dienophiles in the Lewis acid-catalyzed heterocycloadditions with methyl benzylidenepyruvate 1. Good selectivities were observed with cyclohexanone derivatives. Using Eu(fod)3, the dienophile 2b led to the expected endo adduct 3b (93-97%). When using SnCl4, the major product (89-95%) was found to be the 'abnormal' adduct 5b with a trans ring junction.
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.
A base-promoted deprotection of 1,3-dioxolanes to ketones
Yuan, Changchun,Yang, Li,Yue, Guizhou,Yu, Tianzi,Zhong, Weiming,Liu, Bo
supporting information, p. 6972 - 6976 (2013/01/15)
An effective deprotection methodology of dioxolanes was developed, affording moderate to excellent yield via a LTMP-promoted reaction in THF, which displays admirable chemoselectivity in the presence of dimethylketal, 1,3-dioxane, 1,3-dithiane, or other acid-sensitive protective groups.
