565455-73-4Relevant 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 (2007/10/03)
(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.
A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate
Kanomata, Nobuhiro,Maruyama, Satoshi,Tomono, Katsuhito,Anada, Shinnosuke
, p. 3599 - 3603 (2007/10/03)
A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate.
