Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity.

TitlePalladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity.
Publication TypeJournal Article
Year of Publication2013
AuthorsMartínez C, Wu Y, Weinstein AB, Stahl SS, Liu G, Muñiz K
JournalThe Journal of organic chemistry
Volume78
Issue12
Pagination6309-15
Date Published2013 Jun 21
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.

DOI10.1099/ijs.0.056010-0
Alternate JournalJ. Org. Chem.