A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters

Abstract

Crafting chiral boron building blocks Carbon-boron bonds are easily transformed into a wide variety of C–C, C–N, and C–O bonds. With that flexibility in mind, Schmidt et al. show that nickel complexes can catalyze asymmetric alkylation of carbon centers adjacent to boron. This protocol creates chiral alkylboronates that function as stable precursors to numerous complex molecules. The reaction proceeds in stereo-convergent fashion—forming a single product from either mirror image of the α-haloboronate reagent. Successive reactions can also create chains of adjacent chiral alkyl centers with stereochemistry set by the configuration of the ligand bound to nickel. Science , this issue p. 1265