1.
Chirality
; 22(9): 844-8, 2010 Oct.
Article
in English
| MEDLINE
| ID: mdl-20803749
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.