60669-65-0

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 108-94-1 cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 30076-98-3 (3,3-dimethoxypropyl)benzene 
• 17814-55-0 trichloro<(1-cyclohexenyl)oxy>silane 
• 822-87-7 2-Chlorocyclohexanone 
• 22780-11-6 1-(2,2,2-trichloroacetoxy)cyclohexene 
• 17874-17-8 cyclohex-1-enyl-trimethyl-silane 

Downstream Products

• 134273-09-9 (E)-2-(3-phenylpropylidene)cyclohexanone 

Relevant academic research and scientific papers

Engineered Artificial Carboligases Facilitate Regioselective Preparation of Enantioenriched Aldol Adducts

Controlling regio- A nd stereoselectivity of aldol additions is generally challenging. Here we show that an artificial aldolase with high specificity for acetone as the aldol donor can be reengineered via single active site mutations to accept linear and cyclic aliphatic ketones with notable efficiency, regioselectivity, and stereocontrol. Biochemical and crystallographic data show how the mutated residues modulate the binding and activation of specific aldol donors, as well as their subsequent reaction with diverse aldehyde acceptors. Broadening the substrate scope of this evolutionarily na?ve catalyst proved much easier than previous attempts to redesign natural aldolases, suggesting that such proteins may be excellent starting points for the development of customized biocatalysts for diverse practical applications.

Asymmetric aldol reaction catalyzed by a chiral phosphine-silver complex

A catalytic asymmetric aldol reaction of alkenyl trihaloacetates or a γ,δ-unsaturated δ-lactone with aldehydes or an α-keto ester was achieved by using a 2,2′-bis(diphenylphosphino)-1,1′- binaphthyl·silver trifluoromethanesulfonate complex as the chiral p

Installation of a chiral side chain to a 2-alkylidene-1-cycloalkan-1-ol unit by using allylic substitution

The allylic substitution of optically active exocyclic allylic esters of cyclopentane and cyclohexane with ArMgBr-based copper reagents (Ar = aryl) was examined. ArMgBr/Cu(acac)2 in a 2:1 ratio was an adequate reagent to produce the anti-SN2' products efficiently in terms of regioselectivity (95-99a€‰%), chirality transfer (91-99a€‰%), and yield (71-91a€‰%). The Ar groups that were successfully installed include Ph and p-tolyl, those with electron-donating (i.e., p-MeOC6H4) and electron-withdrawing groups (i.e., p-FC6H4), and those with sterically demanding groups (i.e., o-tolyl, o-MeOC6H 4). In an examination of an alkyl reagent, BuMgBr/CuBr·Me 2S in a 2:1 ratio in the presence of ZnI2 afforded the product with high regioselectivity (99a€‰%) and in good yield (91a€‰%). The allylic substitution of exocyclic allylic picolinates (n = 1, 2; R = Ph(CH2)2, iPr, Ph) with a ArCu(acac)MgBr reagent (Ar = Ph, p-tolyl, p-MeOC6H4, p-FC6H4, o-tolyl, o-MeOC6H4) that was derived from a 2:1 ratio of ArMgBr and Cu(acac)2 efficiently afforded the anti-SN2' products in terms of regioselectivity (95-99a€‰%), chirality transfer (91-99a€‰%), and yield (71-91a€‰%). Copyright

N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: A practical proline mimetic for facilitating enantioselective aldol reactions

(Chemical Equation Presented) A highly practical and readily available proline surrogate has been developed with improved solubility properties in common, nonpolar organic solvents. This sulfonamide-based catalyst has proven highly effective at facilitati

Chiral phosphine oxide BINAPO as a Lewis base catalyst for asymmetric allylation and aldol reaction of trichlorosilyl compounds

Chiral phosphine oxide BINAPO, which was readily prepared from chiral phosphine BINAP, exhibited good catalytic activities in the reaction of trichlorosilyl compounds via hypervalent silicate intermediates. The allylation of aldehydes with allyltrichloros

Reactive barium-promoted Reformatsky-type reaction of α- chloroketones with aldehydes

A Reformatsky-type aldol reaction of α-chloroketones with aldehydes has been achieved using reactive barium as a low-valent metal in THF; this one-pot process is more effective for obtaining the desired β-hydroxy ketones in high yields than the stepwise process in which barium enolates are prepared prior to the reaction with aldehydes.

Crossed aldol reaction using cross-linked polymer-bound lithium dialkylamide

Cross-linked polymer-bound lithium dialkylamides were employed in crossed aldol reaction of various carbonyl compounds with aldehydes to afford the corresponding β-hydroxycarbonyl compounds. The introduction of spacer chains to the polymer-bound lithium d

Crossed aldol reaction using polymer-bound lithium amides

Polymer-bound lithium amides were used in an aldol reaction. The introduction of a spacer between the polymer backbone and the reactive site was important to enhance yields of the aldol products. The polymer-bound reagent was repeatedly used in the same r

A high yield procedure for the Me3SiNTf2-induced carbon-carbon bond-forming reactions of silyl nucleophiles with carbonyl compounds: The importance of addition order and solvent effects

We demonstrate the efficiency of Me3SiNTf2 (0.3-1.0 mol%) as a strong Lewis acid catalyst for the Mukaiyama aldol and Sakurai-Hosomi allylation reactions, and that the slow addition of carbonyl compounds to a solution of acid catalys

Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects

Trichlorosilyl enolates of ketones (enoxytrichlorosilanes) were demonstrated to be highly reactive aldol addition reagents. Trichlorosilyl enolates of cyclohexanone (E-enolate) and propiophenone (Z-enolate) reacted readily at room temperature with a wide