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Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity.
|Title||Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity.|
|Publication Type||Journal Article|
|Year of Publication||2013|
|Authors||Martínez C, Wu Y, Weinstein AB, Stahl SS, Liu G, Muñiz K|
|Journal||The Journal of organic chemistry|
|Date Published||2013 Jun 21|
A modified protocol has been identified for Pd-catalyzed intermolecular aminoacetoxylation of terminal and internal alkenes that enables the alkene to be used as the limiting reagent. The results prompt a reassessment of the stereochemical course of these reactions. X-ray crystallographic characterization of two of the products, together with isotopic labeling studies, show that the amidopalladation step switches from a cis-selective process under aerobic conditions to a trans-selective process in the presence of diacetoxyiodobenzene.
|Alternate Journal||J. Org. Chem.|