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

Abstract

Convergent coupling Metal-catalyzed coupling of two flat aromatic rings is one of the most versatile and widely applied chemical reactions. Efforts to extend this protocol to alkyl-alkyl coupling are complicated by the prospect of forming two different three-dimensional configurations at each carbon center, corresponding to four possible products. Huo et al. now report that a chiral nickel catalyst can convergently link two mirror-image pairs of alkyl reactants into just one product (see the Perspective by Xu and Watson). The specific reaction couples propargylic halides to zinc-activated aliphatic amides. Science , this issue p. 559 ; see also p. 509