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  • Title: Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles.
    Author: Huo H, Gorsline BJ, Fu GC.
    Journal: Science; 2020 Jan 31; 367(6477):559-564. PubMed ID: 32001652.
    Abstract:
    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 SN1 and SN2 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 (β-zincated amides) to form carbon-carbon bonds in doubly stereoconvergent processes, affording a single stereoisomer of the product from two stereochemical mixtures of reactants.
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