133270-75-4

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 133817-05-7 ((1-ethoxy-2-methylprop-1-en-1-yl)oxy)triethylsilane 
• 31469-16-6 1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene 
• 600-00-0 ethyl 2-bromoisobutyrate 
• 97-62-1 Ethyl isobutyrate 
• 53807-80-0 ethyl lithioisobutyrate 
• 207446-12-6 2-dimethylsilanyl-2-methyl-propionic acid ethyl ester 
• 30076-98-3 (3,3-dimethoxypropyl)benzene 

Downstream Products

• 130822-13-8 3-hydroxy-2,2-dimethyl-5-phenylpentanoic acid 
• 1376112-28-5 2,2-dimethyl-5-phenylpentan-3-olide 

Relevant academic research and scientific papers

Enantioselective aldol reaction using bornane-2,3-diol-aluminum complex as a chiral Lewis acid

β-Hydroxy ester was formed in high enantiomeric excess by the reaction of ketene silyl acetal with aldehyde in the presence of a chiral Lewis acid prepared from diethylaluminum chloride and chiral diol derived from (+)-camphor.

Scope and mechanism of the electrochemical Reformatsky reaction of α-haloesters on a graphite powder cathode in aqueous anolyte

Six α-haloesters and eighteen carbonyl compounds were submitted to electrochemical coupling on a graphite powder cathode using aqueous anolyte free of organic solvents. Preparative yields of coupling products could be obtained with ethyl 2-bromoisobutyrate and aromatic aldehydes. Ethyl 2-bromopropionate was much less efficient. Extensive variation of applied potential, electrolyte composition, stoichiometry, catalyst, leaving halogen and activating substituents on the carbonyl compound led to the conclusion that the reaction mechanism in most cases proceeds via a radical intermediate generated from the halide reduction. Ethyl chloroacetate produced only trace amounts of coupling product, most probably by a carbanionic mechanism.

1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadienes as strong salt-free reductants for generating low-valent early transition metals with electron-donating ligands

Electron-rich organosilicon compounds, such as 1,4-bis(trimethylsilyl)-1,4- diaza-2,5-cyclohexadiene (2a), 2,5-dimethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2, 5-cyclohexadiene (2b), 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2, 5-cyclohexadiene (

MNBA-mediated β-lactone formation: Mechanistic studies and application for the asymmetric total synthesis of tetrahydrolipstatin

Various β-lactones were prepared from β-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

Metal chloride-promoted aldol reaction of α-dimethylsilylesters with aldehydes, ketones, and α-enones

In the presence of a catalytic amount of LiCl, α-dimethylsilylesters (α-DMS-esters) 1 smoothly reacted with various aldehydes at 30°C to give aldols in good to high yields. On the other hand, the aldol reaction with ketones was effectively promoted by MgCl2 rather than by LiCl. α-Enones also underwent the metal chloride-promoted addition of 1 at the carbonyl carbon or β-carbon. Georg Thieme Verlag Stuttgart.

Uncatalyzed aldol reaction using a dimethylsilyl enolate and α- dimethylsilyl ester in N,N-dimethylformamide

Dimethylsilyl enolates and α-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction.

Reformatsky Reaction in Water: Evidence for a Radical Chain Process

The Reformatsky reaction of 2-bromo esters and carbonyl compounds in the presence of zinc can be carried out in concentrated aqueous salt solutions without any cosolvent. The reaction of bromoacetates is greatly enhanced by catalytic amounts of benzoyl peroxide or peracids and gives satisfactory yields with aromatic aldehydes. Preparative yields comparable to those of the traditional procedure are obtained with ethyl 2-bromoisobutyrate. This ester needs no catalyst and reacts even with saturated aldehydes and aromatic ketones, although in low yields. A radical chain mechanism, initiated by electron abstraction from the organometallic Reformatsky reagent, is proposed. Two nonchain pathways, involving radicals directly produced on the metal surface, may compete, especially in the case of secondary and tertiary halides.

The catalytic asymmetric aldol reaction of silyl ketene acetals with aldehydes in the presence of a chiral borane complex. Nitroethane as a highly effective solvent for catalytic conditions

Catalytic asymmetric aldol reactions of silyl ketene acetals with aldehydes in the presence of 20 mol % of the chiral borane reagent, prepared in situ from the p-nitrobenzenesulfonamide of (S)-valine and BH3-THF complex, gave β-hydroxy carboxylic acid esters in good chemical yields along with excellent enantioselectivity under conditions that employ nitroethane as an effective solvent.

ACTIVATION OF KETENE SILYL ACETALS BY 10-METHYLACRIDINIUM PERCHLORATE: A NOVEL CATALYSIS IN MUKAIYAMA REACTION

10-Methylacridinium perchlorate (1) effectively promotes various reactions of ketene silyl acetals: aldol and Michael addition products are obtained with aldehydes, ketones, acetals, and α-enones.The reactions exhibit unusual dependency upon 1, namely the yields are excellent when a catalytic amount of 1 is employed whereas no desired products are accessible by the use of 1 in a stoichiometric quantity.A novel catalytic cycle is proposed.