Difference in the behavior of methyl (S)-α-bromopropionate in its addition to trimethylvinylsilane depending on the method of initiation

Article abstract of DOI:10.1007/BF01435804

The addition of methyl (S)-2-bromopropionate to trimethylvinylsilane initiated by systems based on iron pentacarbonyl affords a racemic adduct and is accompanied by racemization of the unreacted chiral ester. In the presence of benzoyl peroxide, the reaction proceeds similarly, but no racemization of the starting chiral ester occurs.