91024-55-4

Usage

Chemical compound

2-Propenoic acid, 2-cyano-3-hydroxy-3-phenyl-, ethyl ester

Upstream product

• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 105-56-6 ethyl 2-cyanoacetate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 98-88-4 benzoyl chloride 
• 108-86-1 bromobenzene 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 

Relevant academic research and scientific papers

Palladium-Catalyzed Carbonylative α-Arylation of tert -Butyl Cyanoacetate with (Hetero)aryl Bromides

A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and dicyclohexylmethylamine for the deprotonation step, an excellent functional group tolerance was ensured for the methodology. Through the use of 13C-labeled carbon monoxide generated from 13COgen, the corresponding 13C-isotopically labeled β-ketonitriles were obtained, and these products could subsequently be converted into cyanoalkynes and 3-cyanobenzofurans with site specific 13C-isotope labeling. (Chemical Equation Presented).

Simple access to highly functional bicyclic γ- and δ-lactams: Origins of chirality transfer to contiguous tertiary/quaternary stereocenters assessed by DFT

This paper describes the synthesis of both polysubstituted oxazolo-pyrrolidinones and -piperidinones by a domino process. The methodology is based on the reaction between hydroxyl halogenoamides and Michael acceptors, which leads efficiently to bicyclic lactams. The process is compatible with unsymmetrical electron-withdrawing groups on the Michael acceptor, which allows the formation of two contiguous and fully controlled tertiary and quaternary stereocenters. In the case of tetrasubstituted Michael acceptors, two adjacent quaternary stereocenters are formed in good yield. Starting from (R)-phenylglycinol derived amides results in the formation of enantioenriched bicyclic lactams in low to good yields and with high levels of stereo-selectivity, thus greatly increasing the scope and interest of this strategy. The origins of chirality transfer and diastereoselectivity were studied by DFT calculations and have been attributed to a kinetic control in one of the last two steps of the reaction sequence. This selectivity is dependent upon both the substituents on the Michael acceptor and the sodium cation chelation.

PhICl2-mediated conversion of enamines into α, N -dichloroimines and their reverse conversion mediated by zinc in methanol

Treatment of enamine compounds with iodobenzene dichloride (PhICl 2) conveniently gives a variety of α,N-dichloroimines in high yields. This approach allows the double insertion of the chloro moiety, which is postulated to take place via the io

Electrophilic α-cyanation of 1,3-dicarbonyl compounds

Electrophilic α-cyanation of activated methylene compounds was achieved under mild basic conditions using commercially available TsCN as a CN+ equivalent. A series of 1,3-dicarbonyl compounds, both cyclic and acyclic, were found to be suitable substrates for this transformation. Subjecting 1,1,1-trifluoro-1,3-dicarbonyl compounds to a modified procedure resulted in the formation of α-cyano ketones after trifluoroacetyl group fragmentation. An efficient one-pot cyanation/pyrazole formation sequence to 4-cyano pyrazoles from 1,3-diketones has also been developed. The Royal Society of Chemistry 2013.

3-Cyano-2-(N-cyanoimino)thiazolidine (3-cyano-NCT): An efficient electrophilic cyanating agent for activated methylene compounds

We found that 3-cyano-2-(N-cyanoimino)thiazolidine (3-cyano-NCT) is a novel electrophilic cyanating agent. Various activated methylene compounds were cyanated in moderate to good yields.

ACYLATION OF ACTIVE METHYLENE COMPOUNDS VIA PALLADIUM COMPLEX-CATALYZED CARBONYLATIVE CROSS-COUPLING OF ORGANIC HALIDES

New procedures for acylation of active methylene compounds via palladium complex-catalyzed carbonylation of organic halides are disclosed.