title: Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity.
abstract: 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.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), 43007 Tarragona, Spain.
authors.forename: Claudio
authors.initials: C
authors.lastname: Martínez
authors.forename: Yichen
authors.initials: Y
authors.lastname: Wu
authors.forename: Adam B
authors.initials: AB
authors.lastname: Weinstein
authors.forename: Shannon S
authors.initials: SS
authors.lastname: Stahl
authors.forename: Guosheng
authors.initials: G
authors.lastname: Liu
authors.forename: Kilian
authors.initials: K
authors.lastname: Muñiz
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003903:Deuterium; D007462:Iodobenzenes / Q000737:chemistry*; D007553:Isotope Labeling; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007462:Iodobenzenes; D010165:Palladium; D003903:Deuterium; D010100:Oxygen