Racemization in suzuki couplings: a quantitative study using 4-hydroxyphenylglycine and tyrosine derivatives as probe molecules.

@article{Prieto2007RacemizationIS,
  title={Racemization in suzuki couplings: a quantitative study using 4-hydroxyphenylglycine and tyrosine derivatives as probe molecules.},
  author={M{\`o}nica Prieto and Silvia Mayor and Katy Rodr{\'i}guez and Paul Lloyd-Williams and Ernest Giralt},
  journal={The Journal of organic chemistry},
  year={2007},
  volume={72 3},
  pages={1047-50}
}
Reaction conditions considered to be typical in Suzuki couplings can cause significant (up to 34% of the unwanted enantiomer) loss of optical purity in sensitive substrates such as hydroxyphenylglycine 1. This may be remedied using sodium succinate instead of sodium carbonate as base, but chemical yields are somewhat lower. Optically pure biaryl amino acids… CONTINUE READING