Enantioselective catalytic 1,2-boronate rearrangements

Asymmetric carbon coupling at boron The Matteson reaction produces carbon–carbon bonds by coupling halocarbons such as widely available dichloromethane with an alkyl substituent on boron. Sharmaet al . report asymmetric catalysis of this reaction. Their catalyst, derived from a chiral thiourea, a boronic ester, and an alkyl lithium base, appears to accelerate a chloride abstraction step through its lithium center. The product, still bearing a chloride, can be further modified through stereospecific displacement to generate a wide variety of trisubstituted chiral centers. —JSY