title: Enantioselective and Regiodivergent Functionalization of N-Allylcarbamates by Mechanistically Divergent Multicatalysis.
abstract: A pair of mechanistically divergent multicatalytic reaction sequences has been developed consisting of nickel-catalyzed isomerization of N-allylcarbamates and subsequent phosphoric-acid-catalyzed enantioselective functionalization of the resulting intermediates. By appropriate selection of reaction partners, in situ generated imines and ene-carbamates are mechanistically partitioned to yield opposing functionalized products. Formal α-functionalization to give protected α-arylamines is achieved upon enantioselective Friedel-Crafts reaction with arene nucleophiles, whereas formal β-functionalization is achieved upon reaction with diarylimine electrophiles in an enantioselective Povarov-[4+2] cycloaddition.
authors.affiliation: Institut de Science et d'Ingénierie Supramoleculaires (ISIS), Centre International de Recherche aux Frontières de la Chimie (icFRC), Université de Strasbourg, CNRS, 8 allée Gaspard Monge, 67000, Strasbourg, France.
authors.forename: Edward
authors.initials: E
authors.lastname: Richmond
authors.affiliation: Institut de Science et d'Ingénierie Supramoleculaires (ISIS), Centre International de Recherche aux Frontières de la Chimie (icFRC), Université de Strasbourg, CNRS, 8 allée Gaspard Monge, 67000, Strasbourg, France.|Department of Chemistry, Quaid i Azam University, Islamabad, 45320, Pakistan.
authors.forename: Ismat Ullah
authors.initials: IU
authors.lastname: Khan
authors.affiliation: Institut de Science et d'Ingénierie Supramoleculaires (ISIS), Centre International de Recherche aux Frontières de la Chimie (icFRC), Université de Strasbourg, CNRS, 8 allée Gaspard Monge, 67000, Strasbourg, France. moran@unistra.fr.
authors.forename: Joseph
authors.identifier: http://orcid.org/0000-0002-7851-6133
authors.initials: J
authors.lastname: Moran
keywords: Brønsted acids; carbamates; imines; isomerization; multicatalysis; nickel