60669-59-2Relevant academic research and scientific papers
Chemoselective Two-Directional Reaction of Bifunctionalized Substrates: Formal Ketal-Selective Mukaiyama Aldol Type Reaction
Yanai, Hikaru,Sasaki, Yuichi,Yamamoto, Yuki,Matsumoto, Takashi
, p. 2457 - 2461 (2015/10/19)
In the presence of an acidic zwitterion bearing a highly stabilized carbanion, reactions of ω,ω-dialkoxy carbonyl compounds with ketene silyl acetals (KSA) resulted in an unusual molecular transformation; substitution reaction with the KSA at the ketal mo
The Mukaiyama aldol and Mukaiyama-Michael reactions promoted by commercially available molecular sieves
Anada, Masahiro,Washio, Takuya,Watanabe, Yudai,Hashimoto, Shunichi
experimental part, p. 1489 - 1503 (2010/10/20)
The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4 molecular sieves (4 MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles
One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf
Downey, C. Wade,Johnson, Miles W.,Tracy, Kathryn J.
, p. 3299 - 3302 (2008/09/19)
(Chemical Equation Presented) Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are
Organotin perfluorooctanesulfonates as air-stable Lewis acid catalysts: Synthesis, characterization, and catalysis
An, De Lie,Peng, Zhihong,Orita, Akihiro,Kurita, Akinobu,Man-E, Sumiyo,Ohkubo, Kei,Li, Xingshu,Fukuzumi, Shunichi,Otera, Junzo
, p. 1642 - 1647 (2007/10/03)
The reactions of 1,3-dichloro-1,1,3,3-tetrabutyldistannoxane and di-alkyltin dihalides with silver perfluoro-octanesulfonate provided the corresponding sulfonates as hydrates. The number of water molecules (n) of hydration was dependent on the conditions. The distannoxane derivative was identified as n from 0.5 to 6, while in the hydrated mononuclear species and DMSO complexes n varied widely from 4 to 13. 119Sn NMR spectroscopy and conductivity measurements indicated the ionic dissociation of these compounds in solution. These compounds exhibited unusually high solubility in polar organic solvents. The ionic dissociation together with facile hydration probably causes the unusual solubility. The Lewis acidity of these compounds was found to be high among organotin derivatives on the basis of ESR spectra of Superoxide/ metal-ion complexes. In contrast to well-known organotin Inflates, these compounds suffered no hydrolysis upon storage in open air. The high catalytic activity of the distannoxane 1 was exemplified for various carboncarbon bond-forming reactions, such as Mukaiyama-aldol as well as -Michael reactions and allylation of aldehydes.
Synthesis of 3-Alkoxyalkanoic Esters from Acetals. A Novel Application of Reformatsky Reagents in Asymmetric Synthesis
Basile, Tiziana,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 305 - 311 (2007/10/02)
3-Alkoxyalkanoic esters are directly obtained in high yield from the reaction of acetals with Reformatsky reagents in the presence of titanium(IV)chloride or diethyl ether-boron trifluoride complex in dichloromethane.The reaction of ethyl 4-bromo-2-buteno
Condensation of Reformatsky Reagents with Acetals in the Presence of TiCl4: a Novel Entry to Enantiomerically-enriched β-Hydroxy-esters
Basile, Tiziana,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 596 - 597 (2007/10/02)
3-Alkoxy esters are prepared in high yield from the reaction of ethyl zinc-bromoacetate and acetals in the presence of TiCl4 under very mild conditions; using chiral acetals the corresponding 3-hydroxy esters have been obtained in fair enantiomeric excess.
Reactivity of α-Metal(group 4) Esters. Lewis Acid Mediated Reactions of α-Triphenyltin Esters with Aldehydes and Acetals
Kiyooka, Syun-ichi,Nakata, Masumi
, p. 721 - 722 (2007/10/02)
Ethyl triphenylstannylacetate and ethyl α-triphenylstannylpropionate reacted with aldehydes and acetals to give β-hydroxy and β-alkoxy esters at room temperature in the presence of TiCl4 in moderate yields.Under these conditions ethyl triphenylgermylacetate and ethyl trimethylsilylacetate did not work.
