344258-89-5Relevant academic research and scientific papers
Rhodium-Catalysed coupling of allylic, homoallylic, and bishomoallylic alcohols with aldehydes and n-tosylimines: Insights into the mechanism
Ahlsten, Nanna,Martin-Matute, Belen
supporting information; experimental part, p. 2657 - 2666 (2010/02/28)
The isomerisation of alkenols followed by reaction with aldehydes or N-tosylimines catalysed by rhodium complexes has been studied. The catalytically active rhodium complex is formed in situ from commercially available (cyclooctadiene)rhodium(I) chloride dimer [Rh(COD)Cl]2. The tandem process affords aldol and Mannich-type products in excellent yields. The key to the success of the coupling reaction is the activation of the catalysts by reaction with postassium tert-butoxide (t-BuOK), which promotes a catalytic cycle via alkoxides rather than rhodium hydrides. This mechanism minimises the formation of unwanted by-products. The mechanism has been studied by 1H NMR spectroscopy and deuterium labelling experiments.
Increased lewis acidity in hafnium-substituted polyoxotungstates
Boglio, Cecile,Micoine, Kevin,Remy, Pauline,Hasenknopf, Bernold,Thorimbert, Serge,Lacote, Emmanuel,Malacria, Max,Afonso, Carlos,Tabet, Jean-Claude
, p. 5426 - 5432 (2008/02/09)
Monolacunary polyoxotungs-tates [α1-P2W 17O61]10 and [α-PW11O 39]10 react with HfGl4 to yield [α1-HfP2W17O61]su
Dynamic structural change of the self-assembled lanthanum complex induced by lithium triflate for direct catalytic asymmetric aldol-Tishchenko reaction
Horiuchi, Yoshihiro,Gnanadesikan, Vijay,Ohshima, Takashi,Masu, Hyuma,Katagiri, Kosuke,Sei, Yoshihisa,Yamaguchi, Kentaro,Shibasaki, Masakatsu
, p. 5195 - 5204 (2007/10/03)
The development of a direct catalytic asymmetric aldol-Tishchenko reaction and the nature of its catalyst are described. An aldol-Tishchenko reaction of various propiophenone derivatives with aromatic aldehydes was promoted by [LaLi3(binol)sub
Aqueous asymmetric Mukaiyama aldol reaction catalyzed by chiral gallium Lewis acid with trost-type semi-crown ligands
Li, Hui-Jing,Tian, Hong-Yu,Wu, Yan-Chao,Chen, Yong-Jun,Liu, Li,Wang, Dong,Li, Chao-Jun
, p. 1247 - 1256 (2007/10/03)
The combination of Ga(OTf)3 with chiral semi-crown ligands (1a-e) generates highly effective chiral gallium Lewis acid catalysts for aqueous asymmetric aldol reactions of aromatic silyl enol ethers with aldehydes. A ligand-acceleration effect was observed. Water is essential for obtaining high diastereoselectivity and enantioselectivity. The p-phenyl substituent in aromatic silyl enol. ether (2 h) plays an important role and increases the enantioselectivity up to 95% ee. Although aliphatic silyl enol ethers provided low enantioselectivities and silylketene acetal is easily hydrolyzed in aqueous alcohol, the aldol reactions of silylketene thioacetal (12) with aldehydes in the presence of gallium-Lewis acid catalysts give the β-hydroxy thioester with reasonable yields and high diastereo- (up to 99:1) and enantioselectivities (up to 96% ee).
METHOD FOR ALDOL REACTION IN WATER
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Page 5-6, (2008/06/13)
A method for aldol reaction in water, which comprises: reacting an aldehyde with a silyl enol ether in an aqueous medium in the presence of a boronic acid represented by the following general formula (1):R1R2BOH (wherein R1/sup
Ruthenium-catalyzed tandem olefin migration/aldol and Mannich-type reactions in water and protic solvents
Wang, Mingwen,Yang, Xiao-Fan,Li, Chao-Jun
, p. 998 - 1003 (2007/10/03)
Cross-coupling between 3-buten-2-ol (2) and aldehyde in the presence of a catalytic amount of [RuCl2(PPh3)3] has been developed, through a tandem olefin migration/aldol reaction in a water/toluene mixture. The presence of
Catalytic asymmetric aldol reactions in aqueous media using chiral bis-pyridino-18-crown-6 - Rare earth metal triflate complexes
Hamada, Tomoaki,Manabe, Kei,Ishikawa, Shunpei,Nagayama, Satoshi,Shiro, Motoo,Kobayashi, Sho
, p. 2989 - 2996 (2007/10/03)
Catalytic asymmetric aldol reactions in aqueous media have been developed using Pr(OTf)3 and chiral bis-pyrdino-18-crown-6 1. In the asymmetric aldol reaction using rare earth metal triflates (RE(OTf)3) and 1, slight changes in the i
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 (2007/10/03)
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
Use of boron enolates in water. The first boron enolate-mediated diastereoselective aldol reactions using catalytic boron sources
Mori, Yuichiro,Kobayashi, Juta,Manabe, Kei,Kobayashi, Shi
, p. 8263 - 8268 (2007/10/03)
Highly diastereoselective aldol reactions in water using a catalytic amount of diarylborinic acid have been developed. The reactions proceeded smoothly in the presence of a small amount of an anionic surfactant and a Br?nsted acid. Water was the most suit
Calix[6]arene derivatives bearing sulfonate and alkyl groups as surfactants in Sc(OTf)3-catalyzed Mukaiyama aldol reactions in water
Tian, Hong-Yu,Chen, Yong-Jun,Wang, Dong,Zeng, Cheng-Chu,Li, Chao-Jun
, p. 2529 - 2532 (2007/10/03)
Amphiphilic calix[6]arene derivatives 1a-b were found to be efficient surfactants for Sc(OTf)3-catalyzed Mukaiyama aldol reaction of silyl enol ethers with aldehydes in water. The results indicated that a hydrophobic microenvironment was formed
