84466-82-0Relevant academic research and scientific papers
ENANTIOSELECTIVE CROSS ALDOL REACTION VIA DIVALENT TIN ENOLATE
Iwasawa, Nobuharu,Mukaiyama, Teruaki
, p. 1441 - 1444 (1982)
Highly enantioselective cross aldol reaction between aromatic ketones and various aldehydes is achieved via divalent tin enolates employing chiral diamines derived from (S)-proline as ligands.
Iron-Modified Mesoporous Silica as an Efficient Solid Lewis Acid Catalyst for the Mukaiyama Aldol Reaction
Xu, Wan,Ollevier, Thierry,Kleitz, Freddy
, p. 1932 - 1944 (2018/03/13)
Fe-MCM-41 and Fe-SBA-15, two different iron-containing mesoporous silicas, were successfully synthesized by a straightforward and versatile method using iron acetylacetonate as a metal precursor. pH adjustment with ammonia during the synthesis was found t
Iron(II)-derived lewis acid/surfactant combined catalysis for the enantioselective mukaiyama aldol reaction in pure water
Lafantaisie, Mathieu,Mirabaud, Anais,Plancq, Baptiste,Ollevier, Thierry
, p. 2244 - 2247 (2014/08/18)
The catalytic asymmetric Mukaiyama aldol reaction in pure water was performed by using a combination of iron(II) dodecyl sulfate, a chiral bipyridine ligand, and benzoic acid. By using the obtained iron(II)-derived Lewis acid/surfactant combined catalyst,
Synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by ru(η5-C5Ph5)(CO)2Cl
Bartoszewicz, Agnieszka,Jezowska, Martina M.,Laymand, Kevin,Moebus, Juri,Martin-Matute, Belen
experimental part, p. 1517 - 1530 (2012/06/15)
An efficient method for the synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by Ru(η5-C 5Ph5)(CO)2Cl is described. The influence of the stereoelectronic properties of the catalyst on the reaction outcome has been studied. Optimization of the reaction conditions supressed the formation of undesired side products such as saturated ketones, benzyl alcohols, and α,β-unsaturated ketones. Several aromatic and aliphatic allylic alcohols have been reacted with a large variety of aldehydes or imines to produce β-hydroxy ketones or β-amino ketones, respectively, in yields up to 99a%. Based on experimental data, a mechanism via ruthenium alkoxides and ruthenium aldoxides is proposed. In addition, a C-bound ruthenium enolate has been characterized. β-Hydroxy and β-amino ketones are synthesized from allylic alcohols and aldehydes or imines, respectively. The coupling reaction is catalyzed by Ru(η5-C5Ph5)(CO) 2Cl. Mechanistic investigations support a mechanism via ruthenium alkoxide intermediates.
Efficient synthesis of β-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates
Bartoszewicz, Agnieszka,Livendahl, Madeleine,Martin-Matute, Belen
supporting information; experimental part, p. 10547 - 10550 (2009/12/01)
A study was conducted to demonstrate the synthesis of β-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates. KOtBu was added to a mixture of complex Ru, containing a cyclopentadienyl ligand bearing five phenyl groups. It was demonstrated that ruthenium chloride reacts with KOtBu, forming a ruthenium tert-butoxide complex. It was also demonstrated that the reaction of the tert-butoxide complex with allylic alcohol produced a new alkoxide, as detected by H NMR spectroscopy.
Method for Performing Aldol Reaction in Water
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Page/Page column 4, (2008/06/13)
An aldol reaction in an aqueous solution between an aldehyde represented by the following formula (I): [in-line-formulae]R—CHO??(I) [/in-line-formulae] (wherein R is a hydrocarbon group which may have an substituent), and a silicon enolate represented by
Iron(II) and zinc(II) complexes with designed pybox ligand for asymmetric aqueous Mukaiyama-aldol reactions
Jankowska, Joanna,Paradowska, Joanna,Rakiel, Bartosz,Mlynarski, Jacek
, p. 2228 - 2231 (2007/10/03)
An iron(II) complex with a hindered hydroxyethyl-pybox (he-pybox) ligand shows improved catalytic activity and enantioselectivity for asymmetric Mukaiyama-aldol reactions in aqueous media. This water-stable chiral Lewis acid promotes condensation of aroma
Asymmetric mukaiyama-aldol reaction in aqueous media promoted by zinc-based chiral lewis acids
Mlynarski, Jacek,Jankowska, Joanna
, p. 521 - 525 (2007/10/03)
Asymmetric aldol reactions in aqueous media have been realized by using zinc-based chiral Lewis acids. The aldol products have been obtained with high yield, diastereocontrol and a good level of enantioselectivity. The reactivity of both acetophenone and
TRANSIENT TITANIUM ENOLATE ALDOL CONDENSATIONS
Harrison, Charles R.
, p. 4135 - 4138 (2007/10/02)
A convenient method is described for the generation and subsequent reaction of a proposed titanium enolate with aromatic aldehydes.
SYNTHETIC CONTROL LEADING TO CHIRAL COMPOUNDS
Mukaiyama, Teruaki,Iwasawa, Nobuharu,Stevens, Rodney W.,Haga, Toru
, p. 1381 - 1390 (2007/10/02)
A highly diastereoselective cross aldol reaction is developed using divalent tin enolates formed from stannous trifluoromethanesulfonate and carbonyl compounds.The reaction is extended to a highly enantioselective cross aldol reaction employing chiral dia
