title: (S)-6-Bromo-BINOL-based phosphoramidite ligand with C(1) symmetry for enantioselective hydrogenation and allylic substitution.
abstract: (S)-6-Br-BINOL-derived phosphoramidite, a simple monodentate ligand with a stereogenic center at the phosphorus atom, was synthesized for the first time. This stereoselector generated a high level of enantioselectivity (80-95% ee) in the rhodium-catalyzed hydrogenation of alpha-dehydrocarboxylic acid esters and was also successfully employed in the asymmetric palladium-catalyzed allylic substitution of (E)-1,3-diphenylallyl acetate. The optical yield also showed significant dependence with reaction type: up to 70% ee for allylic amination, up to 75% ee for allylic sulfonylation, and up to 90% ee for allylic alkylation.
authors.affiliation: Department of Chemistry, Ryazan State University, Ryazan, Russian Federation. k.gavrilov@rsu.edu.ru
authors.forename: Konstantin N
authors.initials: KN
authors.lastname: Gavrilov
authors.forename: Eduard B
authors.initials: EB
authors.lastname: Benetsky
authors.forename: Vladimir E
authors.initials: VE
authors.lastname: Boyko
authors.forename: Eugenie A
authors.initials: EA
authors.lastname: Rastorguev
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Davankov
authors.forename: Benjamin
authors.initials: B
authors.lastname: Schäffner
authors.forename: Armin
authors.initials: A
authors.lastname: Börner