102285-85-8Relevant academic research and scientific papers
A new halogen-exchange reaction between Sn-F and Li-X: Selective 1,2- and 1,4-reductions of α,β-unsaturated ketones and effects of halogen substituents on the regioselectivity of organotin hydrides
Moriuchi-Kawakami, Takayo,Matsuda, Haruo,Shibata, Ikuya,Miyatake, Masato,Suwa, Toshihiro,Baba, Akio
, p. 465 - 470 (1999)
We have found that halogen-exchange occurs effectively between Sn-F and Li-X (X = I, Br, Cl) in tin hydride reagents. This fact induced a complete change in the regiochemistry in the reductions of α,β-unsaturated ketones 1 with Bu2SnH2-Bu2SnF2 (Reagent A): the use of Reagent A in combination with HMPA performed 1,2-reductions, while the addition of LiI to Reagent A achieved 1,4-reductions. It was demonstrated that the regioselectivity of organotin hydrides greatly depends on the properties of the halogen substituents attached to tin atoms.
Chiral dendritic bis(oxazoline) copper(II) complexes as Lewis acid catalysts for enantioselective aldol reactions in aqueous media
Yang, Bai-Yuan,Chen, Xiao-Min,Deng, Guo-Jun,Zhang, Yi-Li,Fan, Qing-Hua
, p. 3535 - 3538 (2003)
A series of copper(II) complexes, with chiral bis(oxazoline) ligands disubstituted at the carbon atom linking the two oxazolines by Fréchet-type polyether dendrimers, have been designed and synthesized. These complexes were used as Lewis acid catalysts in
Hydrophobic polymer-supported scandium catalyst for carbon-carbon bond-forming reactions in water
Iimura, Shinya,Manabe, Kei,Kobayashi, Shu
, p. 7673 - 7678 (2004)
It has been revealed that a hydrophobic polymer-supported scandium(III) catalyst prepared from sulfonated polystyrene resin is an effective catalyst for carbon-carbon bond-forming reactions such as Mukaiyama aldol reactions in water. According to studies
TiCl4/Bu3N/(catalytic TMSOTf): Efficient agent for direct aldol addition and claisen condensation
Yoshida, Yoshihiro,Hayashi, Ryosuke,Sumihara, Hiromasa,Tanabe, Yoo
, p. 8727 - 8730 (1997)
TiCl4/Bu3N conducts highly efficient cross aldol additions between different ketones and between ketones and aldehydes, in good to excellent yields with high syn-stereoselectivities. As an extension, direct Claisen condensation between methyl esters was also promoted by TiCl4/Bu3N with 0.05 equiv of TMSOTf co-catalyst.
Iron(III) chloride as a water-compatible lewis acid for diastereoselective aldol reactions in water in the presence of a surfactant
Aoyama, Naohiro,Manabe, Kei,Kobayashi, Shu
, p. 312 - 313 (2004)
Diastereoselective aldol reactions of various aldehydes with silicon enolates in water have been successfully carried out using iron(III) chloride and a surfactant. Contrary to previous understanding, iron(III) chloride has been shown to be a water-compat
Reformatsky-type reaction of α-haloketones promoted by titanium tetraiodide
Shimizu, Makoto,Kobayashi, Fumiko,Hayakawa, Ryuuichirou
, p. 9591 - 9595 (2001)
Titanium(IV) tetraiodide induces a Reformatsky-type reaction of α-iodoketones with carbonyl compounds to give β-hydroxy ketones in good to high yields.
A chiral iron(II)-pybox catalyst stable in aqueous media. Asymmetric Mukaiyama-aldol reaction
Jankowska, Joanna,Paradowska, Joanna,Mlynarski, Jacek
, p. 5281 - 5284 (2006)
Among various transition metals, iron is nontoxic, cheap and hence of great potential synthetic use. We report herein a water stable chiral Lewis acid containing an iron(II) ion and a pybox-type ligand. The resulting cationic aqua complex of C2
Polymer-micelle incarcerated scandium as a polymer-supported catalyst for high-throughput organic synthesis
Takeuchi, Masahiro,Akiyama, Ryo,Kobayashi, Shu
, p. 13096 - 13097 (2005)
A novel immobilization technique for Sc(OTf)3, a polymer-micelle incarcerated (PMI) method, has been developed. PMI Sc(OTf)3 is highly active in several fundamental carbon-carbon bond-forming reactions. The catalyst is recovered quan
Reexamination of CeCl3 and InCl3 as activators in the diastereoselective mukaiyama aldol reaction in aqueous media
Munoz-Muniz, Omar,Quintanar-Audelo, Martina,Juaristi, Eusebio
, p. 1622 - 1625 (2003)
A search for suitable reaction conditions in Mukaiyama-type aldol condensations activated by CeCl3 and InCl3 revealed that the reaction proceeds best in i-PrOH/ H2O (95:5). Contrary to literature precedent, no reaction was
A NEW CONVERSION OF SILYL ENOL ETHERS INTO THE CORRESPONDING BORON ENOLATES WITH DIALKYLBORON HALIDES OR DIALKYLBORON TRIFLATES, AND CROSS ALDOL REACTIONS VIA THE BORON ENOLATES
WADA, Makoto
, p. 153 - 156 (1981)
Silyl enol ethers react with dialkylboron halides or dialkylboron triflates to give the corresponding boron enolates quantitatively under mild conditions.Boron enolates thus generated are effectively used to afford cross aldol products with benzaldehyde.
