Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles.
basic_science · Level V
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- Record sourced from PubMed, PMID 32001652.
- Also identified by DOI 10.1126/science.aaz3855 and PMC identifier 7566878.
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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 S<sub>N</sub>1 and S<sub>N</sub>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 (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.