Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis.

@article{LaroucheGauthier2011AteCO,
  title={Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis.},
  author={Robin Larouche-Gauthier and Tim G. Elford and Varinder K Aggarwal},
  journal={Journal of the American Chemical Society},
  year={2011},
  volume={133 42},
  pages={
          16794-7
        }
}
The addition of an aryllithium reagent to a secondary boronic ester leads to an intermediate boron-ate complex that behaves as a chiral nucleophile, reacting with a broad range of electrophiles with inversion of stereochemistry. Depending on the electrophile, the C-B bond can be converted into C-I, C-Br, C-Cl, C-N, C-O, and C-C, all with very high levels of stereocontrol. This discovery now adds a new, readily available, configurationally stable, chiral organometallic-type reagent to the… CONTINUE READING