73744-66-8Relevant academic research and scientific papers
Stereospecific Palladium-Promoted Oxyamination of Alkenes
Baeckvall, Jan E.,Bjoerkman, Eva E.
, p. 2893 - 2898 (2007/10/02)
A method for direct oxyamination of olefins to vicinal amino alcohol derivatives is described. The reaction proceeds via an aminopalladation-oxidation sequence.Terminal olefins give good yields (60-80percent) whereas internal olefins give lower yields (20-60percent).The oxyamination reaction is stereospecific as shown by reaction of (Z)- and (E)-2-butene and (E)-1-deuterio-1-decene and proceeds by overall cis stereochemistry.The stereochemical outcome is a result of a trans aminopalladation followed by an oxidative cleavage of the palladium carbon bond with inversion of configuration at carbon.Oxidation of the organopalladium ? complex to give an oxidized palladium intermediate, which could be a Pd(IV) intermediate, followed by SN2-type nucleophilic displacement of palladium is the most likely mechanism for the oxidative cleavage reaction.
