145655-36-3Relevant academic research and scientific papers
Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude
Fegyverneki, Dániel,Kolozsvári, Natália,Molnár, Dániel,Egyed, Orsolya,Holczbauer, Tamás,Soós, Tibor
, p. 2179 - 2183 (2019/01/04)
The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.
Access to Multisubstituted 2(5 H)-Furanones Using Hydrogen Bonding-Promoted Ring-Closing Metathesis and Polyamine Workup
Tan, Kai,Yan, Huan,Lu, Pengbo,Liu, Yuehui,Ji, Ruigeng,Liu, Zhongxian,Li, Ya-Min,Yu, Fu-Chao,Shen, Yuehai
, (2019/03/19)
Structurally complex 2(5H)-furanones are potentially challenging targets for ring-closing metathesis (RCM). A hydrogen bonding-guided RCM strategy was developed in this study to provide 3-substituted and 3,4-disubstituted 2(5H)-furanones in moderate to high yields with broad functional group tolerance. A workup procedure using ethylenediamine-derived polyamines such as tetraethylenepentylamine was also established to effectively remove Ru residues in products.
Modular synthesis of optically active lactones by Ru-catalyzed asymmetric allylic carboxylation and ring-closing metathesis reaction
Takii, Koichiro,Kanbayashi, Naoya,Onitsuka, Kiyotaka
scheme or table, p. 3872 - 3874 (2012/05/19)
A new synthetic route to optically active unsaturated γ- and δ-lactones has been demonstrated via asymmetric allylic carboxylation with a planar-chiral Cp′Ru catalyst and ring-closing metathesis reaction with a Grubbs II catalyst, and successfully applied to the enantioselective synthesis of (R)-(-)-massoialactone. The Royal Society of Chemistry 2012.
The catalytic performance of Ru-NHC alkylidene complexes: PCy3 versus pyridine as the dissociating ligand
Krehl, Stefan,Geissler, Diana,Hauke, Sylvia,Kunz, Oliver,Staude, Lucia,Schmidt, Bernd
supporting information; experimental part, p. 1188 - 1198 (2011/03/23)
The catalytic performance of NHC-ligated Ru-indenylidene or benzylidene complexes bearing a tricyclohexylphosphine or a pyridine ligand in ring closing metathesis (RCM), cross metathesis, and ring closing enyne metathesis (RCEYM) reactions is compared. While the PCy3 complexes perform significantly better in RCM and RCEYM reactions than the pyridine complex, all catalysts show similar activity in cross metathesis reactions.
An efficient DABCO-catalyzed Ireland-Claisen rearrangement of allylic acrylates
Li, Yunxia,Wang, Quanrui,Goeke, Andreas,Fráter, Georg
, p. 288 - 292 (2007/10/03)
A novel DABCO-catalyzed Ireland-Claisen [3,3]-rearrangement of allylic acrylates to give α-methylene-γ,δ-unsaturated carboxylic acids in the presence of an excess of TMSCl and DBU in refluxing acetonitrile was developed. The protocol provides an easy entry to α-methylene-γ, δ-unsaturated carboxylic acids from allylic alcohols in good yields. Georg Thieme Verlag Stuttgart.
Ring-closing metathesis strategy to unsaturated γ- and δ-lactones: Synthesis of hydroxyethylene isostere for protease inhibitors
Ghosh, Arun K.,Cappiello, John,Shin, Dongwoo
, p. 4651 - 4654 (2007/10/03)
Ring-closing olefin metathesis of acrylates derived from allylic and homo allylic alcohols in the presence of the Grubbs' catalyst (10-15 mol%) and titanium isopropoxide (0.3-3 equiv) provided ready access to α, β- unsaturated γ and δ-lactones and an important dipeptide isostere intermediate.
