title: Diastereoselective palladium-catalyzed arylcyanation/heteroarylcyanation of enantioenriched N-allylcarboxamides.
abstract: A diastereoselective Pd-catalyzed arylcyanation/heteroarylcyanation of chiral N-allylcarboxamides using Zn(CN)2 as the cyanide source is reported. Nitrile-containing dihydroisoquinolinone products are obtained in good to excellent yields with up to >95:5 dr and with full preseveration of enantioenrichment. By circumventing a difficult nucleophilic cyanation of a hindered neopentyl iodide, this approach represents an improvement to the previously reported formal synthesis of (+)-corynoline.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , Toronto M5S 3H6, Canada.
authors.forename: Hyung
authors.initials: H
authors.lastname: Yoon
authors.forename: David A
authors.initials: DA
authors.lastname: Petrone
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens