Phosphinite Thioethers Derived from Chiral Epoxides. Modular <i>P</i>,<i>S</i>-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions
Xisco Caldentey
Miquel A. Pericàs
10.1021/jo100223w.s003
https://acs.figshare.com/articles/dataset/Phosphinite_Thioethers_Derived_from_Chiral_Epoxides_Modular_i_P_i_i_S_i_Ligands_for_Pd_Catalyzed_Asymmetric_Allylic_Substitutions/2776093
A new family of modular <i>P</i>,<i>S</i>-ligands has been prepared from enantiopure arylglycidols. These ligands have been iteratively optimized with respect to four different structural parameters for use in Pd-catalyzed allylic substitutions. As a final output, highly active and enantioselective ligands for these synthetically important transformations have been developed, and the factors controlling their catalytic behavior have been rationalized. From a methodological point of view, a convenient procedure for the regioselective ring-opening of <i>cis</i>-glycidic esters with bulky thiols to yield the corresponding β-alkylthio-α-hydroxy carboxylic acids has been developed.
2010-04-16 00:00:00
esters
Allylic
carboxylic
enantioselective ligands
acid
iteratively optimized
regioselective
Asymmetric
allylic
synthetically
Modular
alkylthio
factor
thiol
parameter
transformation
enantiopure arylglycidols
SubstitutionsA
substitution
Chiral Epoxides
Phosphinite Thioethers Derived
procedure