Carbon-carbon bond formation in organic chemistry is most commonly controlled by the ubiquitous Grignard reagent, RMgX. This simple formula is an oversimplification, with solvation, oligomerization, and disproportionation complicating matters. However, recently base free monomeric organo magnesium compounds have been prepared (l). The metal environment is controlled by the sterically bulky tris(pyrazolyl)hydroborate ligand, HB(3-Bu-t-pz)3.

Our research efforts have focused on the chiral tris(pyrazolyl)hydroborate ligand, HB(menthylpz)3 (2).

Preparation of the homochiral organomagnesium compound (2) has thus been realized, and we report here our investigations into its carbon-carbon bond formation chemistry with asymmetric control.

 

References

  1. R. Han and G. Parkin, J. Am. Chem. Soc. 1992, 114, 748.
  2. D. D. LeCloux and W. B. Tolman, J. Am. Chem. Soc. 1993, 115, 1153.