177018-34-7

Upstream product

• 100-52-7 benzaldehyde 
• 1165952-91-9 cyclohexa-1,3-diene 
• 1521-51-3 rac-3-bromocyclohexene 
• 18139-74-7 (+/-)-3-trichlorosilylcyclohexene 
• 3413-44-3 (R)-2-cyclohexen-1-ol 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 3352-93-0 (S)-2-cyclohexenyl benzoate 
• 110-83-8 cyclohexene 

Relevant academic research and scientific papers

Catalytic asymmetric allylation of aldehydes with alkenes through allylic C(sp3)-H functionalization mediated by organophotoredox and chiral chromium hybrid catalysis

We describe a hybrid system that realizes cooperativity between an organophotoredox acridinium catalyst and a chiral chromium complex catalyst, thereby enabling unprecedented exploitation of unactivated hydrocarbon alkenes as precursors to chiral allylchromium nucleophiles for asymmetric allylation of aldehydes. The reaction proceeds under visible light irradiation at room temperature, affording the corresponding homoallylic alcohols with a diastereomeric ratio >20/1 and up to 99% ee. The addition of Mg(ClO4)2 markedly enhanced both the reactivity and enantioselectivity.

(+)-Camphor-mediated kinetic resolution of allylalanes: a strategy towards enantio-enriched cyclohex-2-en-1-ylalane

An efficient (+)-camphor-mediated kinetic resolution of racemic cyclohex-2-en-1-ylalane is described. This approach provides an enantiomerically enriched form of the alane, in situ available for synthetic uses. Applied to the allylation of aldehydes, this protocol leads to the corresponding homoallylalcohols in a highly enantioselective manner.

Asymmetric hydrosilylation of cyclohexa-1,3-diene with trichlorosilane by palladium catalysts coordinated with chiral phosphoramidite ligands

Chiral phosphoramidite ligands prepared from (S)-binaphthol and various secondary amines were examined for the palladium-catalyzed asymmetric hydrosilylation of cyclohexa-1,3-diene with trichlorosilane. With a sterically demanding phosphoramidite bearing bis(diphenylmethyl)amine, the high enantiomeric excess of 87% was achieved, which is the highest enantioselectivity in the hydrosilylation of cyclohexadiene reported to date. The catalytic activity in the present hydrosilylation was high with all of the ligands employed, while the enantioselectivities varied dramatically depending on the dialkylamine moiety of the phosphoramidite ligand.

A new entry to carbocyclic nucleosides: Oxidative coupling reaction of cycloalkenylsilanes with a nucleobase mediated by hypervalent iodine reagent

(Chemical Equation Presented) A novel method for synthesizing carbocyclic nucleosides was developed. The new synthesis includes a direct coupling reaction of cycloalkenylsilanes with a silylated nucleobase catalyzed by a hypervalent iodine reagent. By app

Asymmetric allylation of aryl aldehydes: Studies on the scope and mechanism of the palladium catalysed diethylzinc mediated umpolung using phosphoramidite ligands

Using modular, monodentate phosphoramidite ligands, enantioselective palladium catalysed diethylzinc mediated allylation of aldehydes was achieved. The scope of the asymmetric C-C bond formation was investigated with respect to nucleophilic and electrophi

Highly selective and robust palladium-catalyzed carbon-carbon coupling between allyl alcohols and aldehydes via transient allylboronic acids

The highly regio- and stereoselective coupling of allyl alcohols with aldehydes could be achieved with 5 mol-% of SeCSe pincer complex catalyst and p-toluenesulfonic acid in the presence of diboronic acid. The transformations have a broad synthetic scope, and the high yields were obtained without the use of an inert atmosphere and carefully dried solvents. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Modification of Chiral Monodentate Phosphine Ligands (MOP) for Palladium-Catalyzed Asymmetric Hydrosilylation of Cyclic 1,3-Dienes

Several MOP ligands 5 containing aryl groups at 2′ position of (R)-2-(diphenylphosphino)-1,1′-binaphthyl skeleton were prepared and used for palladium-catalyzed asymmetric hydrosilylation of cyclic 1,3-dienes 6 with trichlorosilane. Highest enantioselectivity was observed in the reaction of 1,3-cyclopentadiene (6a) catalyzed by a palladium complex (0.25 mol %) coordinated with (R)-2-(diphenylphosphino)-2′-(3,5-dimethyl-4-methoxyphenyl)-1,1′- binaphthyl (5f), which gave (S)-3-(trichlorosilyl)cyclopentene of 90% ee.

Salen as a chiral activator: Anti versus syn switchable diastereoselection in the enantio-selective addition of crotyl bromide to aromatic aldehydes

To be syn or to be anti? This is an 'open' matter! A good degree of syn simple diastereoselection (up to 83:17) and high enantioselectivity (ee values up to 90%) were obtained with the addition of crotyl bromide to aromatic aldehydes promoted by the [Cr(salen)]/Mn/Me3SiCl catalytic system (see scheme, path B). The remarkable degree of syn simple diastereoselection obtained with organochromium reagents can be explained by an open transition state in a chromium-mediated process.