Enantioselective catalytic 1,2-boronate rearrangements

Abstract

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. Sharma et 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