title: Boron-containing enamine and enamide linchpins in the synthesis of nitrogen heterocycles.
abstract: The use of α-boryl enamine and enamide linchpins in the synthesis of nitrogen heterocycles has been demonstrated. Boryl enamines provide ready access to the corresponding α-halo aldehydes, which undergo regioselective annulation to form borylated thiazoles. A condensation/amidation sequence converts α-boryl aldehydes into stable α-boryl enamides without concomitant C → N migration. We also show that palladium-catalyzed cyclization of α-boryl enamides leads to synthetically versatile isoindolones. These molecules can be subsequently used to access polycyclic scaffolds.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: St Denis
authors.forename: Adam
authors.initials: A
authors.lastname: Zajdlik
authors.forename: Joanne
authors.initials: J
authors.lastname: Tan
authors.forename: Piera
authors.initials: P
authors.lastname: Trinchera
authors.forename: C Frank
authors.initials: CF
authors.lastname: Lee
authors.forename: Zhi
authors.initials: Z
authors.lastname: He
authors.forename: Shinya
authors.initials: S
authors.lastname: Adachi
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin