title: Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization.
abstract: In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmetric desymmetrization (enantioselective monohydrodebromination) followed by kinetic resolution of the resulting monobromophenyl products (up to 99% ee). The enantioselectivity strongly depended on the substituent (R2) at the C4'position, amount of NaBH4, and reaction temperature.
authors: Department of Applied Chemistry, Shibaura Institute of Technology , 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
authors: Motohiro
authors: M
authors: Hirai
authors: Department of Applied Chemistry, Shibaura Institute of Technology , 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
authors: Shumpei
authors: S
authors: Terada
authors: Department of Applied Chemistry, Shibaura Institute of Technology , 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
authors: Hiroaki
authors: H
authors: Yoshida
authors: Department of Applied Chemistry, Shibaura Institute of Technology , 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
authors: Kenki
authors: K
authors: Ebine
authors: Department of Applied Chemistry, Shibaura Institute of Technology , 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
authors: Tomoaki
authors: T
authors: Hirata
authors: Department of Applied Chemistry, Shibaura Institute of Technology , 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
authors: Osamu
authors: O
authors: Kitagawa