55291-51-5

Upstream product

• 147795-55-9 ethyl 2-cyano-2-(p-tolyl)acetate 
• 2947-61-7 (4-methylphenyl)acetonitrile 
• 75-26-3 isopropyl bromide 
• 75-30-9 2-iodo-propane 

Downstream Products

• 120352-40-1 2-Isopropyl-5-{[3-(3-methoxy-phenoxy)-propyl]-methyl-amino}-2-p-tolyl-pentanenitrile 
• 120351-81-7 2-(1-methylethyl)-5-oxo-2-(4-methylphenyl)pentane nitrile 
• 120352-14-9 2-Isopropyl-5-[3-(3-methoxy-phenoxy)-propylamino]-2-p-tolyl-pentanenitrile 
• 125675-52-7 5,5-Diethoxy-2-isopropyl-2-p-tolyl-pentanenitrile 

Relevant academic research and scientific papers

Palladium-Catalyzed Asymmetric α-Arylation of Alkylnitriles

Asymmetric arylation of alkylnitriles forms quaternary stereocenters in good enantiocontrol for the first time. A lithium heterodimer consisting of an alkylnitrile anion and a disilylamide ion is the actual species responsible for the stereodetermining transmetalation in the catalytic cycle.

Enantioselective Rhodium-Catalyzed Allylic Alkylation of Prochiral α,α-Disubstituted Aldehyde Enolates for the Construction of Acyclic Quaternary Stereogenic Centers

A highly enantioselective rhodium-catalyzed allylic alkylation of prochiral α,α-disubstituted aldehyde enolates with allyl benzoate is described. This protocol provides a novel approach for the synthesis of acyclic quaternary carbon stereogenic centers and it represents the first example of the direct enantioselective alkylation of an aldehyde enolate per se. The versatility of the α-quaternary aldehyde products is demonstrated through their conversion to a variety of useful motifs applicable to target-directed synthesis. Finally, mechanistic studies indicate that high levels of asymmetric induction are achieved from a mixture of prochiral (E)- and (Z)-enolates, which provides an exciting development for this type of transformation.

Enantioselective rhodium-catalyzed allylic substitution with a nitrile anion:construction of acyclic quaternary carbon stereogenic centers

A direct and highly enantioselective rhodium-catalyzed allylic alkylation of allyl benzoate with α-substituted benzyl nitrile pronucleophiles is described. This simple protocol provides a new approach toward the synthesis of acyclic quaternary carbon stereogenic centers and provides the first example of the direct asymmetric alkylation of a nitrile anion. The synthetic utility of the nitrile products is amply demonstrated through conversion to various functional groups and the synthesis of a bioactive aryl piperazine in an expeditious four-step sequence.