124267-25-0Relevant academic research and scientific papers
A copper-free palladium catalyzed cross coupling reaction of vinyl tosylates with terminal acetylenes
Fu, Xiaoyong,Zhang, Shuyi,Yin, Jianguo,Schumacher, Doris P.
, p. 6673 - 6676 (2002)
A copper-free palladium-catalyzed cross coupling of vinyl tosylate (2) and terminal acetylenes was investigated, affording a convenient and efficient method for construction of an sp-sp2 carbon-carbon bond. The tosylate (2) derived from 1,3-cyc
Construction of spirofused tricyclic frameworks by NHC-catalyzed intramolecular stetter reaction of a benzaldehyde tether with a cyclic exsnone
Hsu, Day-Shin,Cheng, Chiao-Yun
, p. 10832 - 10842 (2019/09/30)
Various benzaldehyde tethers with a cyclic enone were prepared from commercially available 2-hydroxybenzaldehydes via a three-step sequence involving triflate formation, Sonogashira cross-coupling, and regioselective hydrogenation. These substrates were t
Synthesis and evaluation of novel α-fluorinated (E)-3-((6- methylpyridin-2-yl)ethynyl)cyclohex-2-enone-O-methyl oxime (ABP688) derivatives as metabotropic glutamate receptor subtype 5 PET radiotracers
Sephton, Selena Milicevic,Mu, Linjing,Schibli, Roger,Kraemer, Stefanie D.,Ametamey, Simon M.,Schweizer, W. Bernd
supporting information, p. 7154 - 7162,9 (2020/09/09)
In the search for an optimal fluorine-18-labeled positron emission tomography (PET) radiotracer for imaging metabotropic glutamate receptor subtype 5 (mGluR5), we have prepared a series of five α-fluorinated derivatives based on the ABP688 structural mani
Formation of quaternary stereogenic centers by NHC-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on polyconjugated cyclic enones
Tissot, Matthieu,Poggiali, Daniele,Henon, Helene,Mueller, Daniel,Guenee, Laure,Mauduit, Marc,Alexakis, Alexandre
, p. 8731 - 8747 (2012/09/25)
The copper-catalyzed conjugate addition of various Grignard reagents to polyconjugated enones (dienone and enynone derivatives) is reported. The catalyst system, composed of copper triflate and an NHC ligand, led to the unusual selective formation of the 1,4-addition products. This reaction allows for the creation of all-carbon chiral quaternary centers with enantiomeric excesses up to 99 %. The remaining unsaturation on the 1,4 adducts give access to valuable synthetic transformations. Copyright
Highly enantioselective and regioselective copper-catalyzed 1,4 addition of grignard reagents to cyclic enynones
Tissot, Matthieu,Perez Hernandez, Alexandra,Mueller, Daniel,Mauduit, Marc,Alexakis, Alexandre
, p. 1524 - 1527 (2011/05/04)
In this letter we describe an unusual result in terms of regioselectivity with respect to copper-catalyzed conjugate additions of various Grignard reagents to cyclic enynones. The use of Cu(OTf)2 and NHC ligand L1 as the catalyst combination in CH2Cl2 led to the unique formation of the 1,4 adduct. This selectivity does not follow the general trend previously observed in the literature using extended Michael acceptors. Moreover these reactions allowed for the creation of a quarternary stereogenic center with enantioselectivities up to 97% ee.
Two methods for the preparation of 2-cyclohexenones from resin-bound 1,3-cyclohexanedione
Fraley, Mark E.,Rubino, Robert S.
, p. 3365 - 3368 (2007/10/03)
The addition of organolithium or Grignard reagents to viny]ogous ester resin 1 followed by mild hydrolysis of product resins 2 provides 3-alkyl-2-cyclohexenones in high purity (>95%). Alternatively, conversion of 1 to vinyl triflate resin 4 followed by palladium-mediated couplings with aryl boronic acids and hydrolysis furnishes 3-ary]-2-cyclohexenones in lower yield, but exceptional purity.
