Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles

Stereochemical control in the construction of carbon-carbon bonds between an alkyl electrophile and an alkyl nucleophile is a persistent challenge in organic synthesis. Classical substitution reactions via S(N)1 and S(N)2 pathways are limited in their ability to generate carbon-carbon bonds (inadequate scope, due to side reactions such as rearrangements and eliminations) and to control stereochemistry when beginning with readily available racemic starting materials (racemic products). Here, we report a chiral nickel catalyst that couples racemic electrophiles (propargylic halides) with racemic nucleophiles (beta-zincated amides) to form carbon-carbon bonds in doubly stereoconvergent processes. affording a single stereoisomer of the product from two stereochemical mixtures of reactants.