chiral

copolymers

asymmetric

magnetoresistance

enantioselectivities

dlbcl cell

anther

trait

magnified image

copolyesters

cross coupling

nickel catalyzed

regio

growth charts

conjugate addition

oxidative addition

enantioenriched

cruzi infection

Science

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.

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