565455-72-3Relevant academic research and scientific papers
Hammett studies of enantiocontrol by PHOX ligands in Pd-catalyzed allylic substitution reactions
Constantine, Ryan N.,Kim, Naomi,Bunt, Richard C.
, p. 2279 - 2282 (2003)
(Matrix presented) Electronically modified PHOX ligands 3a-e were synthesized to probe the mechanism of the enantioselective palladium-catalyzed allylic alkylation and amination reactions. Alkylation with dimethyl sodiomalonate produced only a small variation in the ee (89.3% to 93.4%), but amination with benzylamine gave a much wider variation in the ee (16.4% to 66.6%). Hammett analysis suggests that the substituents interact more significantly with phosphorus and supports a combined electronic and steric basis for enantioselection.
