(S)-6-Bromo-BINOL-based phosphoramidite ligand with C(1) symmetry for enantioselective hydrogenation and allylic substitution.
(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.
Gavrilov
Konstantin N
KN
Department of Chemistry, Ryazan State University, Ryazan, Russian Federation. k.gavrilov@rsu.edu.ru
Benetsky
Eduard B
EB
Boyko
Vladimir E
VE
Rastorguev
Eugenie A
EA
Davankov
Vadim A
VA
Schäffner
Benjamin
B
Börner
Armin
A