title: An Alkoxide Anion Triggered tert-Butyloxycarbonyl Group Migration. Mechanism and Application.
abstract: We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.
authors.affiliation: Department of Chemistry, Department of Biochemistry, Molecular Biology, and Cell Biology, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, USA.
authors.forename: Fengtian
authors.initials: F
authors.lastname: Xue
authors.forename: Richard B
authors.initials: RB
authors.lastname: Silverman