339314-78-2

Upstream product

• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 120-92-3 cyclopentanone 
• 1921-90-0 (E)-2-benzylidenecyclopentanone 
• 75-24-1 trimethylaluminum 
• 139080-04-9 2-(Hydroxy-phenyl-methyl)-2-methyl-cyclopentanone 
• 1120-72-5 2-Methylcyclopentanone 
• 98-86-2 acetophenone 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 139080-12-9 2-[1-Phenyl-eth-(Z)-ylidene]-cyclopentanone 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 672-65-1 (1-chloroethyl)benzene 

Relevant academic research and scientific papers

Branched-Selective Direct α-Alkylation of Cyclic Ketones with Simple Alkenes

Herein, we describe an intermolecular direct branched-selective α-alkylation of cyclic ketones with simple alkenes as the alkylation agents. Through an enamine-transition metal cooperative catalysis mode, the α-alkylation is realized in an atom- and step-economic manner with excellent branched selectivity for preparing β-branched ketones. Employment of a pair of bulky Br?nsted acid and base as additives is responsible for enhanced efficiency. Promising enantioselectivity (74 % ee) has been obtained. Experimental and computational mechanistic studies suggest that a pathway through alkene migratory insertion into the Ir?C bond followed by C?H reductive elimination is involved for the high branched selectivity.

Branched-selective intermolecular ketone α-alkylation with unactivated alkenes via an enamide directing strategy

We describe a strategy for intermolecular branched-selective α-alkylation of ketones using simple alkenes as the alkylating agents. Enamides derived from isoindolin-1-one provide an excellent directing template for catalytic activation of ketone α-positions. High branched selectivity is obtained for both aliphatic and aromatic alkenes using a cationic iridium catalyst. Preliminary mechanistic study favors an Ir-C migratory insertion pathway.

Copper-Catalyzed Asymmetric Conjugate Addition to α-Alkylidene Cycloalkanones

The asymmetric copper-catalyzed conjugate addition to α-alkylidene cycloalkanones, substituted at their terminal position with aromatic and aliphatic groups, is reported. While high enantioselectivity is reached using chiral phosphoramidite ligands, with R3Al reagents, moderate diastereoselectivity was observed upon hydrolysis of the aluminium enolates. A Grignard reagent also react with high diastereoselectivity.

Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers

The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.

Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide

Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of α-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl chloride, and allylsilane or alkynylsilane.

The Reaction of 2-Substituted Cycloalkanones with Aldehydes under Acidic Conditions

The title reaction proceeded with either ring enlargement or bicyclic compound formation, as well as the aldol reaction, depending upon the types of the reactants and reaction conditions.

Regioselective Lewis Acid-mediated α-sec-Alkylation of Carbonyl Compounds

Carbonyl compounds such as ketones, aldehydes, acyloins, or carboxylic esters can be alkylated at the α-position via the corresponding O-silylated forms using activated alkyl halides or acetates in the presence of Lewis acids.In the case of unsymmetricall