Meng F, McGrath KP, Hoveyda AH * Boston College, Chestnut Hill, USA
Multifunctional Organoboron Compounds for Scalable Natural Product Synthesis.
Nature 2014;
513: 367-374
Key words
boron - multicomponent reaction - copper
Significance
The authors demonstrate the generation of multifunctional alkenylboron fragments starting
from two simple unsaturated organic molecules and a commercially available diboron
reagent. These fragments were shown to carry several advantageous properties. The
catalyst used is generated in situ by the reaction of inexpensive CuCl with a chiral
ligand which was prepared on multigram scale in good yield.
Comment
The practical protocol can be performed on large scale and makes gram quantities of
a variety of complex organic molecules easily available. The products, which contain
a stereogenic carbon center, a monosubstituted alkene, and an easily functionalizable
Z-trisubstituted alkenylboron group, are obtained in good yields and excellent selectivities.
