1140518-47-3

Upstream product

• 119-58-4 4,4'-bis(dimethylamino)benzhydrol 
• 123-38-6 propionaldehyde 
• 90-94-8 bis(p-dimethylaminophenyl)methanone 

Downstream Products

• 1140518-58-6 (S)-2-(3,6-bis(dimethylamino)-9H-xanthen-9-yl)propan-1-ol 

Relevant academic research and scientific papers

A catalytic reactor for the organocatalyzed enantioselective continuous flow alkylation of aldehydes

The use of immobilized metal-free catalysts offers the unique possibility to develop sustainable processes in flow mode. The challenging intermolecular organocatalyzed enantioselective alkylation of aldehydes was performed for the first time under continu

Accelerating Amine-Catalyzed Asymmetric Reactions by Intermolecular Cooperative Thiourea/Oxime Hydrogen-Bond Catalysis

The ability of intermolecular cooperative thiourea/oxime hydrogen-bond catalysis for improving and accelerating asymmetric aminocatalysis is presented. The two readily available hydrogen-bond-donating catalysts operates in synergy with a chiral amine catalyst to accomplish highly stereoselective transformations. The synergistic catalyst systems simultaneously activate both electrophiles and nucleophiles, and make the transformations more chemo- and stereoselective. This was exemplified by performing co-catalytic enantioselective direct intermolecular α-alkylation reactions of aldehydes, direct aldol reactions, and asymmetric conjugate reactions, which gave the corresponding products in high yields and enantiomeric ratios.

A rational approach towards a new ferrocenyl pyrrolidine for stereoselective enamine catalysis

Ironing out the details: Proline and pyrrolidine derivatives (Hayashi- J?rgensen catalysts) are considered work horses in organocatalysis. This report describes a new effective ferrocenyl pyrrolidine catalyst that is able to perform well in benchmark organocatalytic reactions (see figure). The ferrocene moiety controls the conformational space and a simple alkyl group effectively covers a face of the derived enamine. This new framework can find applications in organocatalysis, and in general, in new ligand design. Copyright

The acid free asymmetric intermolecular α-alkylation of aldehydes in fluorinated alcohols

The acid free asymmetric intermolecular α-alkylation of aldehydes with alcohols has been discovered using trifluoroethanol as solvent. This unprecedented system affords the enantioenriched functionalized primary alcohols (after NaBH4 reduction) in high yields and good to excellent enantioselectivities with wide substrate scope in the absence of any acid additive.

Organocatalytic stereoselective α-alkylation of aldehydes with stable carbocations

The organocatalytic stereoselective alkylation of aldehydes is carried out with the four stable carboca-tions 1-4 in the presence of a catalytic amount (20mol%) of MacMillan imi-dazolidinones 5-6. In all reactions, luti-dine was used as a base. The alkylation reactions are investigated at different temperatures with linear and branched aldehydes. In the case of carbocation tropylium fluoroborate, an interesting reversal of alkylation product configuration was observed, which is driven by entropic effects in the reaction. The absolute configuration of the products obtained is determined by chemical correlation and found to be in general agreement with the model proposed by MacMillan to justify the stereoselectiv-ity obtained in the reactions promoted by catalysts of type 5-6.

Functionalized chiral ionic liquid catalyzed asymmetric SN1 α-alkylation of ketones and aldehydes

Pyrrolidine-derived functionalized chiral ionic liquids (FCILs) have been found to catalyze asymmetric SN1 α-alkyl-ations of ketones and aldehydes with up to 99% yield, >99:1 dr and 87% ee. The FCIL catalysts enable SN1 α-alkylations

Organocatalytic asymmetric alkylation of aldehydes by SNreaction of alcohols

Work-alcoholic! The elusive enantioselective catalytic α-alkylation of aldehydes, a widely sought transformation, was brought to execution by the use of alcohols capable of forming stabilized carbocations (see scheme, TFA=trifluoroacetic acid).