Concerted Amidation of Activated Esters: Reaction Path and Origins of Selectivity in the Kinetic Resolution of Cyclic Amines via N-Heterocyclic Carbenes and Hydroxamic Acid Cocatalyzed Acyl Transfer was written by Allen, Scott E.;Hsieh, Sheng-Ying;Gutierrez, Osvaldo;Bode, Jeffrey W.;Kozlowski, Marisa C.. And the article was included in Journal of the American Chemical Society in 2014.Recommanded Product: 1722-95-8 This article mentions the following:
The N-heterocyclic carbene and hydroxamic acid cocatalyzed kinetic resolution of cyclic amines generates enantioenriched amines and amides with selectivity factors up to 127. In this report, a quantum mech. study of the reaction mechanism indicates that the selectivity-determining aminolysis step occurs via a novel concerted pathway in which the hydroxamic acid plays a key role in directing proton transfer from the incoming amine. This modality was found to be general in amide bond formation from a number of activated esters including those generated from HOBt and HOAt, reagents that are broadly used in peptide coupling. For the kinetic resolution, the proposed model accurately predicts the faster reacting enantiomer. A breakdown of the steric and electronic control elements shows that a gearing effect in the transition state is responsible for the observed selectivity. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Recommanded Product: 1722-95-8).
(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Recommanded Product: 1722-95-8
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem